Category: Tetrahydrofurans

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.219823-47-9,(R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate,as a common compound, the synthetic route is as follows.

Tert-butyl(4-(2-chloro-5-iodobenzyl)phenoxy)dimethylsilane (1 .0 Kg), tetrahydrofuran (6.0 L) and (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl) tetrahydro-2H-pyran-2-one (1 .221 Kg) were charged into a 20 L flask under Nitrogen atmosphere. Toluene (6.0 L) was charged into the flask and the resulted mixture was cooled to -80 C. n-Butyl Lithium in hexane (1 .6M, 2.8 Kg) was added slowly over a period of 3 hours at -80 C. The reaction mixture was maintained for 1 hour at -80 C. A solution of methanesulfonic acid (1 .46 Kg of methanesulfonic acid in 9.0 L of methanol) was added to the reaction mass at -70 C. The reaction mass was heated to -10 C and stirred for 30 minutes and heated to 30 C and stirred for 12 hours at 30 C. The reaction mass was cooled to 5 C and sodium bicarbonate solution (2.0 Kg of sodium bicarbonate in 23 L of water) was added slowly. The reaction mass was stirred for 30 minutes at 30 C. The reaction mass was washed with Toluene (6.0 Lx 3) and the reaction mass was concentrated under vacuum until 20 volumes remains in the flask. The reaction mass was extracted with ethylacetate (10.0 Lx5) and the ethylacetate layer was washed with water (3.0 L). The ethylacetate layer was charged into a 100 L reactor and concentrated under vacuum to 3 volumes remained in the reactor. The concentrated ethylacetate layer was stripped off with acetonitrile (3.0 Lx 3) then dichloromethane (7.0 L) and acetonitrile (1 .2 L) were charged into the reactor and the reaction mass was cooled to -30 C. Triethylsilane (0.57 Kg) and Borontrifluoride etherate solution (1 .307 Kg) were charged into the reactor and the reaction mass was stirred for 3 hours at -30 C. Temperature was raised to -5 C and stirred for 6 hours. A solution of sodium carbonate (2.0 Kg of sodium carbonate in 20.0 L of water) was added to the reaction mass over a period of 30 minutes at 5 C. The reaction mass was heated to 30 C and stirred for 30 minutes. The reaction mass was concentrated under vacuum until 25 volumes remained in the reactor. The mass was washed with toluene (4.0 L) and extracted with ethylacetate (8.0 Lx2 and 4.0 Lx4) and the ethylacetate layer washed with water (2.0 Lx2) The organic layer was concentrated under vacuum until 2 volumes remained in the reactor then the crude mass was stripped off with ethylacetate (3.0 l_x2) and with DMF (1 .4 L). Tosyl-THF (0.634 Kg) and DMF (0.20 L) were charged into the reactor and the resulted mass was stirred for 30 minutes at 30 C. Cesium carbonate lot 1 (0.57 Kg) was added to the reaction mass. Reaction mass was heated to 45 C and stirred for 2 hours at 45 C. Cesium carbonate lot 2 (0.57 Kg) was added to the reaction mass and the reaction mass was stirred for 2 hours. Cesium carbonate lot 3 (0.57 Kg) was added to the reaction mass the reaction mass was stirred for 20 hours at 45 C. The reaction mass was cooled to 30 C and water (4.0 L) was added to the mass and stirred for 30 minutes. Layers were separated and the aqueous layer was washed with toluene (4.0 L). The aqueous layer was concentrated at 70 C under vacuum until 1 .0 volume remained in the reactor. The concentrated mass was cooled to 30 C and water (10.0 L) and acetonitrile 1 .0 L) were charged into the reactor at 30 C and the resulted mixture was heated to 45 C and the mixture was stirred for 6 hours at 45 C. The suspension was cooled to 25 C and stirred for 7 hours at 25 C. The precipitation was filtered and the wet solid was washed with water (3.0L) and the solid was suck dried. The wet compound and DMF (1 .0 L) were charged into another reactor and the solution was heated to 45 C. Acetonitrile (1 .0 L) charged followed by water (10.0 L) into the reactor at 45 C and stirred for 6 hours. The suspension was cooled to 25 C and stirred for 6 hours. The precipitation was fileted and the wet cake was washed with water. The wet material was suck dried. The wet material was dried under vacuum at 60 C for 6 hours to yield 0.55 Kg of crystalline empagliflozin. Purity by HPLC 99%., 219823-47-9

219823-47-9 (R)-Tetrahydrofuran-3-yl 4-methylbenzenesulfonate 13837325, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; DR. REDDY’S LABORATORIES LIMITED; CHAKKA, Ramesh; PATHIVADA, Deepika; PEDDI REDDY, Subba Reddy; IPPALAPALLI, Sandeep; CHINTADA, Krishnarao; KOYA, Ravi Teja; ORUGANTI, Srinivas; BADARLA, Venkata Krishna Rao; DONIPARTHI, Kiran Kumar; SUD, Abhishek; MADAVARAM, Sateesh; LEKKALA, Amarnath Reddy; KUNHIMON, Syam Kumar Unniaran; JAWLEKAR, Suhas; KANDAGATLA, Bhaskar; (72 pag.)WO2017/203457; (2017); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

16874-33-2, Tetrahydrofuran-2-carboxylic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of 0.7 g of tetrahydrofuran-2 – carboxylic acid and 10 ml of THF was added 0.84 g of oxalyl chloride and 0.05 ml of DMF. The mixture was stirred for 2 hours at room temperature, then, THF was distilled off under reduced pressure. To the residue was added 20 ml of THF and 1.02 g of 3-amino-6- (pyridin- 3-yl ) -pyran-2-one , then, 0.91 g of triethylamine was added, and the mixture was stirred for 18 hours at room temperature. Water (10 ml) was added, and about 15 ml of THF was distilled off under reduced pressure, then, the precipitate was filtrated. The filtratedprecipitate was washed with 10 ml of water and 15 ml of hexane, then, drying under reduced pressure wasperformed to obtain 0.88 g of N- [2-oxo-6- (pyridin-3-yl) – 2H-pyran-3-yl ] -tetrahydrofuran-2-carboxamide(hereinafter, referred to as the inventive compound 49) . Inventive compound 491 H-NMR (CDC13) delta: 9.19 (1H, s), 9.03-9.00 (1H, m) , 8.66- 8.63 (1H, m) , 8.42 (1H, d) , 8.10-8.06 (1H, m) , 7.40 (1H, dd) , 6.79 (1H, d) , 4.48 (1H, dd) , 4.14-4.08 (1H, m) , 4.00-3.95 (1H, m) , 2.42-2.32 (1H, m) , 2.19-2.10 (1H, m) , 2.02-1.91 (2H, m) .

16874-33-2, 16874-33-2 Tetrahydrofuran-2-carboxylic acid 86079, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; ARIMORI, Sadayuki; SHUTO, Akira; MIZUNO, Hajime; WO2011/49150; (2011); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.105-21-5,Gamma-heptalactone,as a common compound, the synthetic route is as follows.

gamma-heptalactone was added into an decarboxylation and dimerisation reactor R1, in which the upper layer of the catalyst bed layers was loaded with Amberlyst catalyst (Amberlyst 15WET), and the lower layer of the catalyst bed layers was loaded with the decarboxylation and dimerisation catalyst B produced above, two catalyst layers having a same packing height. Decarboxylation and dimerisation was conducted under conditions of a temperature of 180 degree Celsius and a WHSV of 1.5 h-1, resulting in a conversion of 96%, and a selectivity to C8 olefin of 81%. After separation, the C8 olefin was fed into an aromatization reactor R2 for aromatization under the actions of a temperature of 500 degree Celsius, an aromatization catalyst MCM-22, and a space velocity of 2 h-1, to provide a stream containing a xylene product, with a selectivity to xylene of 94%, and a yield of carbon as xylene of 73.1%. The olefin not reacted completely could be recycled to the dimer reactor for continued reaction. The olefin obtained was further separated to provide light aromatics comprising benzene, toluene and the like, simultaneously providing PX in high-purity. In addition, an additional part was obtained as a heavy component from the column bottom. Hydrogen out of the column top could be used as a raw material for hydrogenating oligomers into gasoline or diesel oil, while the heavy component from the column bottom could be used as a raw material for diesel oil or be combusted to supply heat., 105-21-5

105-21-5 Gamma-heptalactone 7742, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; CHINA PETROLEUM & CHEMICAL CORPORATION; SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY, SINOPEC; KONG, Dejin; ZHENG, Junlin; SONG, Qi; QI, Xiaolan; XU, Xuan; JIANG, Xiangdong; YANG, Deqin; (19 pag.)US2018/282256; (2018); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1679-47-6,3-Methyldihydrofuran-2(3H)-one,as a common compound, the synthetic route is as follows.

Step 1: Preparation of 4-hydroxy-1-(2-chloro-4-methoxyphenyl)-2-methylbutan-1-one To a 1.0 L, 3-neck round bottom flask, equipped with a mechanical stirrer and an internal thermometer, was added a solution of 4-bromo-3-chloroanisole (12.0 g, 54.0 mmol) in 350 mL of THF under nitrogen. The solution was cooled to -85 C. with a MeOH/liquid nitrogen bath. To this solution was added t-BuLi (72.0 mL, 1.6 M in pentane, 122 mmol) slowly followed by the addition of a solution of alpha-methyl-gamma-butyrolactone (9.25 g, 92.0 mmol) in THF (30.0 mL). The internal temperature was controlled <-80 C. After 1 h stirring at <-80 C., the reaction mixture was quenched with saturated NH4Cl solution and warmed to room temperature. Water and EtOAc were added and separated. The aqueous layer was extracted with EtOAc (2*). The combined organic solutions was dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (E:H, 1:3) to give 10.4 g (79%) of brown oil as the title compound: 1H NMR (400 MHz, CDCl3) delta7.53 (d, J=8.6 Hz, 1H), 6.97 (d, J=2.4 Hz, 1H), 6.85 (dd, J=8.6, 2.4 Hz, 1H), 3.88 (s, 3H), 3.77-3.69 (m, 2H), 3.64-3.56 (m, 1H), 2.16-2.07 (m, 1H), 1.76-1.67 (m, 1H), 1.23 (d, J=7.0 Hz, 3H); MS (EI) m/z 241.16 (M+-H). 1679-47-6, As the paragraph descriping shows that 1679-47-6 is playing an increasingly important role.

Reference£º
Patent; Pfizer Inc; US2007/224636; (2007); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.124391-75-9,(S)-(Tetrahydrofuran-3-yl)methanol,as a common compound, the synthetic route is as follows.

Example 64A 3-(tosylmethyl)tetrahydrofuran To a solution of (tetrahydrofuran-3-yl)methanol (1.0 g, 9.8 mmol) in CH2Cl2 (5 mL) and triethylamine (1.98 g, 19.6 mmol) was added p-toluenesulfonyl chloride (2.8 g, 14.7 mmol) in portions over 15 minutes. The mixture was stirred at ambient temperature for 12 hours and was quenched with 10 mL of saturated, aqueous NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2*10 mL) The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound. MS (DCI/NH3) m/z 257 (M+H)+.

124391-75-9, The synthetic route of 124391-75-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ABBOTT LABORATORIES; US2008/153883; (2008); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.104227-71-6,(S)-tert-Butyl (5-oxotetrahydrofuran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

To a solution of the compound obtained in Referential Example 194 (0.87 g) in tetrahydrofuran (20 mL) was added dropwise lithium bis(trimethylsilyl)amide (as 1M tetrahydrofuran solution, 8.65 mL) at -78C, and the thus-obtained mixture was stirred for 30 minutes. Subsequently, a solution of p-toluenesulfonyl azide (1.02 g) in tetrahydrofuran (10 mL) was added thereto, followed by stirring for 5 minutes, and after trimethylchlorosilane (1.7 mL) was added thereto, the thus-obtained mixture was gradually brought back to room temperature while being stirred. After the reaction mixture was stirred for 2 hours, the mixture was diluted with diethyl ether, and the diluted mixture was washed with 10% aqueous HCl, 5% saturated aqueous sodium hydrogencarbonate, and saturated brine, followed by drying over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 4:1), to thereby give the title compound (0.62 g).1H-NMR(CDCl3) delta:1.46(9H, s), 4.09(1H, dt, J=15.3, 7.6Hz), 4.12-4.23(1H, m), 4.37-4.50(1H, m), 4.54(1H, dd, J=9.0, 7.6Hz), 4.81-4.90(1H, m).

104227-71-6, 104227-71-6 (S)-tert-Butyl (5-oxotetrahydrofuran-3-yl)carbamate 10943528, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1577301; (2005); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

204512-95-8, (S)-Tetrahydrofuran-3-amine hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: lambda/-(tert-Butoxycarbonyl)-lambda/-{2-r(3i?)-tetrahvdrofuran-3-ylaminolpropyUglycine (III) To a solution (0.56 M) of (35)-tetrahydrofuran-3-amine.etaCl (prepared as described in HeIv. CHm. Acta 2000, 53, 1825-1845) in DCE were added N-(tert-butoxycarbonyl)-N-(2- oxopropyl)glycine (1.3 eq), DIPEA (1 eq), NaBH(OAc)3 (2 eq), cat. AcOH and cat. NaOAc. Reaction mixture was irradiated at MW for 20 min at 1200C. DCE was removed under reduced pressure and the residue purified by filtration on silica gel eluting of the desired intermediate with EtOAc. Evaporation of the organic solvent yielded (III). MS (ES) C14H26N2O5 requires: 302, found: 303 (M+H)+., 204512-95-8

204512-95-8 (S)-Tetrahydrofuran-3-amine hydrochloride 18664284, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/63244; (2009); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

Production Example 128 (0444) 5-(3-Phenylpropoxymethyl)isoxazole-3-carboxylic acid (0.60 g, 2.3 mmol) was added to chloroform (amylene addition product) (12 mL), and cooled to 0C. Triethylamine (0.48 ml, 3.4 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.66 g, 3.4 mmol) and 1-hydroxybenzotriazole (0.47 g, 3.4 mmol) were added thereto, and the mixture was stirred for 10 minutes. Tetrahydrofuran-3-ylmethylamine (0.26 g, 2.5 mmol) was added to the mixture, and the mixture was stirred at room temperature for 18 hours. Then, water was added thereto, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.31 g of N-(tetrahydrofuran-3-ylmethyl)-5-(3-phenylpropoxymethyl)iso xazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (132)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.70-1.65(m, 1H), 1.96-1.89(m, 2H), 2.10-2.06(m, 1H), 2.59-2.56(m, 1H), 2. 69 (t, 2H), 3.46(t, 2H), 3.52(t, 2H), 3.59-3.57(m, 1H), 3.77-3.73(m, 1H), 3.94-3.79(m, 2H), 4.60(s, 2H), 6.69(s, 1H), 6.94(s, 1H), 7.20-7.16(m, 3H), 7.29-7.27(m, 2H)

184950-35-4, The synthetic route of 184950-35-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

Production Example 269 (0590) 5-(2,4-Difluorobenzyloxymethyl)isoxazole-3-carboxylic acid (1.20 g, 4.5 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.92 g, 6.7 mmol), triethylamine (0.93 mL, 6.7 mmol) and 1-hydroxybenzotriazole (0.06 g, 0.4 mmol) were added to chloroform (amylene addition product) (10 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.03 g, 5.4 mmol) was added to the mixture at room temperature, and the mixture was stirred overnight and then concentrated under reduced pressure. Dilute hydrochloric acid was added to the residue, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated saline water and dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 0.78 g of N-(tetrahydrofuran-3-ylmethyl)-5-(2,4-difluorobenzyloxymeth yl)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (278)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 1.63-1.72 (1H, m), 2.04-2.14 (1H, m), 2.52-2.63 (1H, m), 3.47 (2H, t), 3.59 (1H, dd), 3.73-3.80 (1H, m), 3.83-3.95(2H, m), 4.62(2H, s), 4.68 (2H, s), 6.74(1H, s), 6.81(1H, dt), 6.89(1H, dt), 6.93(1H, br s), 7.35-7.42(1H, m), 184950-35-4

As the paragraph descriping shows that 184950-35-4 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

5- (1-phenylcyclopropyl) isoxazole-3-carboxylic acid chloride ( In toluene solution (20 mL) Tetrahydrofuran-3-ylmethylamine hydrochloride (250 mg, 1.82 mmol) And 1 mol / L sodium hydroxide aqueous solution (20 mL) Were simultaneously added under cooling with ice water. After vigorously stirring for 30 minutes under cooling with ice water, The reaction mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, After drying with anhydrous sodium sulfate, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, Represented by the following equation N- (tetrahydrofuran-3-ylmethyl) -5- (1-phenyl-cyclopropyl) isoxazole-3-carboxamide (Hereinafter referred to as the present amide compound (156)) 504 mg was obtained., 184950-35-4

As the paragraph descriping shows that 184950-35-4 is playing an increasingly important role.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem