Heterocyclic Building Blocks-Tetrahydrofuran

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.,124391-75-9

(1) Tetrahydrofuran-3-ylmethyl 4-methylbenzenesulfonate Tetrahydro-3-furanmethanol (4.09 g) and triethylamine (7.81 mL) were dissolved in tetrahydrofuran (30 mL). p-Toluenesulfonyl chloride (9.53 g) was added under ice-cooling, followed by stirring for one hour. Then, the mixture was heated to room temperature and further stirred for 18 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. Then, the organic layer was sequentially washed with a saturated sodium chloride solution and a saturated sodium bicarbonate solution, dried over magnesium sulfate and filtered. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to obtain the title compound (8.9 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 1.50-1.60 (m, 1H) , 1.96-2.04 (m, 1H), 2.45 (s, 3H), 2.53-2.64 (m, 1H), 3.47-3.51 (m, 1H), 3.65-3.81 (m, 3H), 3.88-3.93 (m, 1H), 3.96-4.00 (m, 1H), 7.32-7.36 (m, 2H), 7.76-7.79 (m, 2H).

As the paragraph descriping shows that 124391-75-9 is playing an increasingly important role.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; EP2017275; (2009); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

1679-47-6, 3-Methyldihydrofuran-2(3H)-one is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1679-47-6

To a 2 L, 3-neck round bottom flask, equipped with a mechanic stirrer and an internal temperature controller, is added a solution of 2,4-dichlorobromobenzene (65.5 g, 290.7 mmol) in 1.1 L [OF THF] under nitrogen. The solution is cooled to-95 C with a [MEOH/LIQUID] nitrogen bath. To this solution is added t-BuLi (400 mL, 1.6 M in pentane, 639.5 mmol) slowly via syringe pump followed by the addition of a solution of [OC-METHYL-Y-BUTYROLACTONE] (43.5 g, 434.8 mmol) in THF (100 mL). The internal temperature is controlled <-80 [C.] After 1 h stirring [<-80 C,] the reaction mixture is quenched with saturated NH4C1 solution and warmed to room temperature. Water (2 L) and EtOAc (1 L) are added and separated. The aqueous layer is extracted with EtOAc (2 x 2 L). The combined organic solutions is dried [(MGSO4)] and filtered. The filtrate is concentrated in vacuo to dryness to give 80.9 g of [1- (2,] 4-dichlorophenyl) -4- hydroxy-2-methylbutan-1-one as light yellow oil. The residue is used for Swern oxidation. To a 2 L, 3-neck round bottom flask, equipped with a mechanic stirrer and an internal temperature controller, is added DMSO (104.1 mL, 1465.7 mmol) and [CH2C12] (1.1 L). The solution is cooled to-80 C with a [MEOH/LIQUID] nitrogen bath. To this solution is added oxalyl chloride (63.9 mL, 732.9 mmol) slowly via syringe pump. The mixture is stirred at-80 C for 15 min followed by the addition of a solution of the above obtained crude [1- (2,] 4-dichlorophenyl) -4-hydroxy-2- methylbutan-1-one in [CH2C12] (150 mL) slowly via syringe pump. After stirring <-70 [C] for 1 h, to the mixture is added [ET3N] (456 mL, 3271.7 mmol). The cooling bath is removed after 5 min and the mixture is stirred at room temperature for 1.5 h. The mixture is diluted with hexanes (6 L) and washed with water (6 L). The aqueous layer is extracted with hexanes (6 L). The combined organic solutions is concentrated in vacuo to dryness and the residue is subjected to column chromatography (silica gel, 1/6 EtOAc/heptane) to give 36 g (50% for two steps) of light yellow oil as the title compound [:'H] NMR (400 MHz, CDCl3) 8 9.86 (s, 1H), 7.61 (d, J= 8.3 Hz, 1H), 7.49 (d, J=2. 0 Hz, 1H), 7.37 (dd, J=2. 0,8. 3 Hz, 1H), 3.81-3. 76 (m, 1H), 3.18 (dd, [J =] 8.2, 18.6 Hz, 1H), 2.65 (dd, [J =] 5.0, 18.6 Hz, 1H), 1.21 (d, [J =] 7.3 Hz, 3H) ; 13C NMR (100 MHz, [CDC13)] [# 206. ] 1,202. 4,139. 5,139. 2,134. 4,132. 7,132. 4,129. 6,48. 8, 42.0, 18.6 ; IR (liq. ) 2974,2936, 1996,1910, 1708,1585, 1457,1374, 1228, [1191,] 1106,1064, 978,828, [810 CM'' ;] MS (CI) [NZLZ] 247 (M+), 245 (M+). As the paragraph descriping shows that 1679-47-6 is playing an increasingly important role. Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/35586; (2004); 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.17347-61-4,2,2-Dimethylsuccinicanhydride,as a common compound, the synthetic route is as follows.,17347-61-4

Example 25 : Preparation of 4-(((l S,3aS,5aR,5bR,7aR,9S, 11 aR, 1 IbR, 13aR, 13bR)-l – isopropyl-3a-((S)-2-(5-(4-metho xyphenyl)-lH-imidazol-2-yl)pyrro lidine- 1 -carbonyl)- 5a,5b,8,8,l la-pentamethylicosahydro-lH-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4- oxobutanoic acid: [0210] To a stirred solution of ((lS,3aS,5aR,5bR,7aR,9S,l laR,l lbR,13aR,13bR)-9- hydroxy- 1 -isopropyl-5 a,5b,8,8, 11 a-pentamethylicosahydro-3aH-cyclopenta[a]chrysen-3a- yl)((S)-2-(5-(4-methoxyphenyl)- lH-imidazol-2-yl)pyrrolidin- 1 -yl)methanone (Example 24- step 2, 0.2 g, 0.29 mmol) and 2,2-dimethyl succinicanhydride (0.14 g, 1.17 mmol) in toluene (6 mL) was added DMAP (0.07 g, 0.58 mmol). The reaction mixture was heated at 90¡ãC for 12 hours. After completion of the reaction (monitored by TLC), reaction mixture was concentrated under reduced pressure, cooled to 0¡ãC, acidified to pH = 6 with IN HC1 and extracted with DCM. The combined organic extracts were washed with water, brine, dried over Na2S04. Then the solvent was evaporated and to the resulting solid was recrystalised from ACN to give the title compound (0.09 g, Yield 26percent) as a white solid. 1H-NMR, CDC13, 300 MHz): delta 7.49- 7.47 (m, 2H), 7.12 (s, 1H), 6.89 (d, J = 8.7 Hz, 2H), 5.36- 5.34 (m, 1H), 4.54- 4.49 (m, 1H), 3.81 (s, 3H), 3.68- 3.56 (m, 2H), 2.94- 2.90 (m, 2H), 2.71- 1.12 (m, 36H), 0.99- 0.84 (m, 18H), 0.72 (d, J = 6.6 Hz, 3H); ESI MS: 812.5 (M+H).

As the paragraph descriping shows that 17347-61-4 is playing an increasingly important role.

Reference£º
Patent; HETERO RESEARCH FOUNDATION; PANDURANGA REDDY, Adulla; PARTHASARADHI REDDY, Bandi; RATHNAKAR REDDY, Kura; VL SUBRAHMANYAM, Lanka; DAVID KRUPADANAM, Gazula, Levi; VENKATI, Mukkera; SUDHAKAR, Neela; SRINIVAS REDDY, Kallem; WO2014/105926; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

17347-61-4, 2,2-Dimethylsuccinicanhydride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,17347-61-4

To a stirred solution of (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy- 5a,5b,8,8,11a-pentamethyl-N-(1-(5-phenyl-1H-imidazol-2-yl)cyclopentyl)-1-(prop-1-en-2-yl)icosahydro-3aH-cyclopenta[a]chrysene-3a-carboxamide (step 2, 0.06 g, 0.09 mmol) and 2,2-dimethyl succinicanhydride (0.046 g, 0.36 mmol) in toluene (4 ml), was added DMAP (0.022 g, 0.18 mmol). The reaction mixture was heated at 90C for about 12 hours. After completion of the reaction (monitored by TLC), the reaction mixture was concentrated under reduced pressure, cooled to 0C, acidified to pH=6 with 1N HCl and extracted with DCM. The combined organic extracts were washed with water, brine, dried over Na2SO4 then the solvent was evaporated under reduced pressure and the resulting solid was recrystallized from ACN to afford the title compound (0.022 g, yield: 31%). 1H NMR (300 MHz, CDCl3): delta 7.65-7.62 (m, 2H), 7.36-7.29 (m, 4H), 4.59 (s, 1H), 4.51 (s, 1H), 4.46-4.38 (m, 1H), 2.93- 2.91 (m, 1H), 2.62-1.31 (m, 32H), 1.26 (s, 3H), 1.22 (s, 6H), 0.86-0.68 (m, 19H); ES Mass: 794.64 [M+H]+.

As the paragraph descriping shows that 17347-61-4 is playing an increasingly important role.

Reference£º
Patent; HETERO RESEARCH FOUNDATION; BANDI, Parthasaradhi Reddy; KURA, Rathnakar Reddy; GAZULA LEVI, David Krupadanam; ADULLA, Panduranga Reddy; NEELA, Sudhakar; MOGILI, Narsingam; (87 pag.)WO2017/21922; (2017); 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.16874-33-2,Tetrahydrofuran-2-carboxylic acid,as a common compound, the synthetic route is as follows.,16874-33-2

Example-3: N-[3-[(4-Amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro- 2-furan carboxamide (Alfuzosin)To a mixture of terahydrofuroic-2-acid (99.7 gm) and dichloromethane (600ml) at 0 to 50C, triethylamine (86.8 gm) was added. To the resulting reaction mixture, ethyl chloroformate (93.2 gm) was added at low temperature. The reaction mixture was further stirred for one hour and a slurry of N]-(4-Amino-6,7-dimethoxyquinazol-2-yl)-Ni-methylpropylenediamine (100 gm) in dichloromethane (400 ml) was added. The resultant mixture was stirred for about one hour for the completion of the reaction and sodium hydroxide solution (500 ml, IN) was added. The layers were separated and the organic layer was washed with sodium hydroxide solution and concentrated under vacuum. The residue thus obtained was stirred with methanol (200 ml) for three hours to get slurry, which was filtered to get alfuzosin base in solid form. The product thus obtained was re-crystallized from methanol to get pure, isolated, solid alfuzosin base. Yield: 75 gm Purity: 99.8percent

The synthetic route of 16874-33-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; WOCKHARDT LTD.; NATHANI, Pankaj Kumar; NARODE, Sunil Dnyaneshwar; SIDDIQUI, Mohammad Jaweed Mukarram; WO2007/69050; (2007); A2;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

696-59-3, 2,5-Dimethoxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,696-59-3

General procedure: Amine (1 mmol), 2,5-dimethoxytetrahydrofuran (1.1 mmol)and L-(+)-tartaric acid-choline chloride based DES (1.5 g) were added to a 50 mL round bottom flask and the reaction mixturewas stirred at 90 C. The progress of the reaction was monitoredby TLC. After completion of the reaction, the mixture was cooled to room temperature and the product was extracted with ethyl acetate.After the evaporation of the solvent, the residue was purified by columnchromatography on silica gel to afford the pure product. The DES wasdried under vacuumand reused for the next cycle.

The synthetic route of 696-59-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Ping; Ma, Fei-Ping; Zhang, Zhan-Hui; Journal of Molecular Liquids; vol. 198; (2014); p. 259 – 262;,
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.696-59-3,2,5-Dimethoxytetrahydrofuran,as a common compound, the synthetic route is as follows.,696-59-3

7a 1-(4-Methylphenyl)pyrrole The title compound was obtained as yellow crystals (10.5 g, 66%, m.p. 82-83 C.) from 4-methylaniline (10.7 g) and 2,5-dimethoxytetrahydrofuran (13.2 g) according to the known methods (R. Jones, C. F. Candy and P. H. Wright, J. Chem. Soc., 1970, 2563).

The synthetic route of 696-59-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5389641; (1995); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

453-20-3,453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydro-furan-3-ol (9.0 g, 79 mmol) and triethyl amine (20 mL, 176 mmol) in THF (200 mL) was added methanesulfonyl chloride (12.9 g, 113 mmol) at 0 C. The mixture was stirred overnight and then evaporated to dryness. The residue was extracted with EtOAc (3*300 mL) and washed with saturated, aqueous NaRCO3. The organic layer was dried over Na2SO4 and evaporated to dryness to give methanesulfonic acid tetrahydro-furan-3-yl ester as a yellow viscous liquid (12.4 g. 94%) which was used without further purification.

As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

Reference£º
Patent; H. Lundbeck A/S; US2012/252853; (2012); 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.

Tetrahydrofuran-3-ylmethylamine hydrochloride (0.20 g, 1.48 mmol) And triethylamine (0.15 g, 1.48 mmol) Was added to chloroform (amylene added product) (8 mL). To the mixture, 5- (2-methyl-3-phenylbenzyl) oxymethyl isoxazole-3-carboxylic acid (0.40 g, 1.24 mmol) at room temperature, 1-Hydroxybenzotriazole (0.02 g, 0.12 mmol) And 1-ethyl-3- (3-dimethylaminopropyl) Carbodiimide hydrochloride (0.28 g, 1.48 mmol) was added, After stirring for 3 hours, Dilute hydrochloric acid was added, It was extracted twice with chloroform. The organic layer was washed with saturated sodium bicarbonate water, After drying with anhydrous sodium sulfate, And concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, The following equationIndicated by N- (tetrahydrofuran-3-ylmethyl) -5- (2-methyl-3-phenylbenzyl) oxymethyl isoxazole-3-carboxamide (Hereinafter referred to as amide compound (123)) 0.38 g was obtained., 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; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
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.13031-04-4,4,4-Dimethyldihydrofuran-2,3-dione,as a common compound, the synthetic route is as follows.

General procedure: Hydrogenations were performed in an atmospheric batch reactor. The catalytic system including catalyst (25 mg) and 5 mL of solvent (toluene or toluene and AcOH mixture) was loaded into the reactor and purged three times with H2. The catalyst was stirred and pre-hydrogenated for 30 min. The calculated amount of modifier was injected and after 0.5-1 min 1 mmol (128 mg) of KPL was added and stirred in the presence of H2 for the required reaction time. Standard conditions were: 25 mg Pt/Al2O3, 5 mL solvent, [modifier] 0.1 mM/L, 0.1 MPa H2 pressure, 294-297 K, ~ 900 rpm (diffusion control free reaction), and 1 mmol (128 mg) of KPL. The product identification and the enantiomeric excess, ee% = |[R] – [S]| ¡Á 100 / ([R] + [S]) were monitored by gas chromatography (HP 6890 N GC-FID using 30 m long Cyclodex-B capillary column, head pressure 21.65 psi He, and column temperature 398 K. Retention times (min): 10.6 of (S)-PL, and 11.2 of (R)-PL. The reproducibility was ¡À 2%., 13031-04-4

As the paragraph descriping shows that 13031-04-4 is playing an increasingly important role.

Reference£º
Article; Szollosi, Gyoergy; Balazsik, Katalin; Bucsi, Imre; Bartok, Tibor; Bartok, Mihaly; Catalysis Communications; vol. 32; (2013); p. 81 – 85;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem