Heterocyclic Building Blocks-Tetrahydrofuran

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

3,3-DIMETHYL-DIHYDRO-FURAN-2,5-dione (6.4g) was heated at [50OC] in ethanol (150 [ML)] overnight. The solvent was removed in vacuo and the residue triturated with hexane to yield 2, [2-DIMETHYL-SUCCINIC] acid 4-ethyl ester (4.66g) which was used without further purification. t-Butanol (7.5 mL) was added to a mixture of 2,2-Dimethyl-succinic acid 4- ethyl ester (2.74g, 15. [7MMOL)] in dichloromethane (62 mL) containing magnesium sulfate (7.5 g) and [CONC.] sulfuric acid (0.85 mL) and the mixture was stirred at room temperature overnight. Saturated sodium bicarbonate solution was added and the product was extracted into dichloromethane, washed with brine solution, dried and concentrated to yield the diested as a colorloess oil (1.89 g). The ethyl ester was hydrolyzed by trating the crude sample with potassium hydroxide (2.75g) in a mixture of ethanol (50 [ML)] and water (25 mL) at room temperatire for 2h. The reaction was acidified using 1N [HC1] [(AQ)] and extracted into ether, dried and concentrated to yield 2,2-Dimethyl-succinic acid [1-TERT-BUTYL] ester (1.4g). This acid was treated under the conditions of Example 320 (step 1) to yield 3- [[3- (3-CHLORO-PHENYL)- [1,] 2,4] oxadiazol-5-yl] -2,2-dimethyl-propionic acid tert-butyl ester (1.9g). This t-Bu ester was deprotected using formic acid (19 mL) at [50¡ãC] for 20 min. The crude product was concentrated and triturated with a mixture of ether and hexane to yield [3- [3- (3-CHLORO-PHENYL)- [1,2,4] [OXADIAZOL-5-YL]-2,] 2-dimethyl-propionic acid (1.12g). To a solution [OF 3- [3- (3-CHLORO-PHENYL)- [1,2,4] oxadiazol-5-yl] -2,2-dimethyl-propionic acid (561 mg, 2 mmol) and triethylamine [(1.] [1] [ML,] 8 mmol) in THF (9 ml), isobutyl chloroformate (0.31 mL, 2.4 mmol) was added dropwise [AT-78 ¡ãC.] After being stirred for lh, hydrazine hydrate (1 mL, 11 mmol) was added. The reaction mixture was stirred at room temperature for 1 h and concentrated. A small amount of ice was added to quence any excess reagent and precipitate the product, which was collected by filtration to give 482 mg of the title compound., 17347-61-4

17347-61-4 2,2-Dimethylsuccinicanhydride 87067, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; ASTRA ZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14881; (2004); A2;,
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4344-84-7, 5-Oxotetrahydrofuran-2-carboxylic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4344-84-7

REFERENCE EXAMPLE 8 Production of 1-t-butyl 2-oxoglutarate [Compound (8)] To a solution of 5.0 g of 5-oxo-2-tetrahydrofurancarboxylic acid in 100 ml of dichloromethane was added 0.3 ml of concentrated sulfuric acid, to which was further added an excess volume (ca. 50 ml) of isobutene. The reaction mixture was left standing overnight at room temperature under tight sealing, which was poured into a cooled saturated aqueous solution of sodium hydrogencarbonate. The dichloromethane layer was separated, washed with water, dried (Na2 SO4) and concentrated to give t-butyl 5-oxo-2-tetrahydrofurancarboxylate as a colorless oily substance. IRnumaxNeat cm-1: 1760. NMR (60 MHz, CDCl3)delta: 1.50(9H, s), 2.4(4H, m), 4.8(1H, m).

4344-84-7 5-Oxotetrahydrofuran-2-carboxylic acid 636468, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US4891427; (1990); A;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.57595-23-0,Methyl 4-oxotetrahydrofuran-3-carboxylate,as a common compound, the synthetic route is as follows.

57595-23-0, To a stirred solution of potassium hydroxide (1.97 g, 31.7 mmol) and 2-methyl-2- thiopseudourea sulfate (4.41 g, 31.7 mmol) in water (15 mL) was added dropwise of methyl tetrahydro-4-oxofuran-3-carboxylate (1.59 g, 15.9 mmol) over 5 min. The mixture was stirred at rt for 3 h and refluxed for 3 h. It was evaporated to dryness to give 4.1 g of crude product and used for next reaction without further purification.

57595-23-0 Methyl 4-oxotetrahydrofuran-3-carboxylate 14666564, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; CYTOVIA, INC.; WO2008/21456; (2008); A2;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem

184950-35-4, (Tetrahydrofuran-3-yl)methanamine hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Production Example 153 (0473) Tetrahydrofuran-3-ylmethylamine hydrochloride (150 mg, 1.09 mmol) and a 1 mol/L aqueous sodium hydroxide solution (8 mL) were simultaneously added to a toluene solution (10 mL) of 5-(benzo[b]thiophen-2-ylmethy)isoxazole-3-carboxylic acid chloride (< 0.38 mmol), under ice-water cooling. The mixture was vigorously stirred for 30 minutes under ice-water cooling, and then the reaction mixture was extracted once 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 104 mg of N-(tetrahydrofuran-3-ylmethyl)-5-(benzo[b]thiophen-2-ylmeth y)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (161)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta(ppm)):1.62-1.71(m, 1H), 2.03-2.13(m, 1H), 2.50-2.63(m, 1H), 3.43-3.48 (m, 2H), 3. 58 (dd, J=8. 9, 5. 3Hz, 1H), 3.72-3.79(m, 1H), 3.82-3.94(m, 2H), 4.41(s, 2H), 6.58(s, 1H), 6.91 (s, 1H), 7.16(s, 1H), 7.29-7.37(m, 2H), 7.69-7.73(m, 1H), 7.76-7.81(m, 1H) 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;,
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16874-33-2, Tetrahydrofuran-2-carboxylic acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of acid 1 (1.0g, 8.9 mmol) in THF (15 mL) was added Et3N (3.1 mL, 22.2 mmol), and T3P (50% solution in EtOAc, 10.6mL, 17.7 mmol) at 0-5 C and the solution was stirred for about 10 min under a nitrogen atmosphere. Then N,O-dimethylhydroxylaminehydrochloride salt (1.1g, 13.3 mmol) was added to the reaction mixture at 0-5 C and the heterogeneous mixture was allowed to stir at room temperature till the completion of the reactionas indicated by TLC (see Table S-1). The mixture was then diluted with water(20 mL) followed by ethyl acetate (20 mL) and stirred for about 10 min. The separated organic layer was collected, washed with 5% citric acid (2 x10 mL),5% Na2CO3 (2 x 10 mL), and then brine solution. The collected organic layer was dried over anhydrous Na2SO4, filtered and concentrated under low vacuum. The crude product obtainedwas purified by flash column chromatography over silicagel (100-200 mesh) using 12-15% EtOAc / n-hexane as eluent to affordthe desired compound., 16874-33-2

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

Reference£º
Article; Jammula, Subba Rao; Anna, Venkateswara Rao; Tatina, Sudhakar; Krishna, Thalishetti; Sreenivas, B. Yogi; Pal, Manojit; Tetrahedron Letters; vol. 57; 35; (2016); p. 3924 – 3928;,
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184950-35-4, (Tetrahydrofuran-3-yl)methanamine hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Production Example 219 (0539) 5-[3-(2-Naphthyl)propyl]isoxazole-3-carboxylic acid (0.56 g, 2.0 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.33 g, 2.4 mmol), triethylamine (0.25 g, 2.4 mmol) and 1-hydroxybenzotriazole (0.03 g, 0.24 mmol) were added to chloroform (amylene addition product) (5 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.46 g, 2.4 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 concentrate, 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 0.49 g of N-(tetrahydrofuran-3-ylmethyl)-5-[3-(2-naphthyl)propyl]isox azole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (228)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.66-1.73(1H, m), 2.06-2.19 (3H, m), 2.54-2.61(1H, m), 2.83-2.87 (4H, m), 3.46 (2H, t), 3.58-3.60(1H, m), 3.75-3.79(1H, m), 3.84-3.94(2H, m), 6.48(1H, s), 6.93(1H, s), 7.32(1H, dd), 7.42-7.49(2H, m), 7.62(1H, s), 7.78-7.83(3H, 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;,
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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 – [(2,2,2-trifluoroethyl) oxymethyl] isoxazole-3-carboxylic acid (0.30 g, 1.3 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.22 g, 1.6 mmol), Triethylamine (0.16 g, 1.6 mmol) And 1-hydroxybenzotriazole (0.02 g, 0.16 mmol) Was added to chloroform (amylene added product) (4 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.31 g, 1.6 mmol) was added at room temperature, After stirring overnight, And concentrated under reduced pressure. Dilute hydrochloric acid was added to the concentrate, 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, The following equationIndicated by N- (tetrahydrofuran-3-ylmethyl) -5 – [(2,2,2-trifluoroethyl) oxymethyl] isoxazole-3-carboxamide (Less than, This amide compound (128) is described. ) 0.32 g was obtained.

184950-35-4, 184950-35-4 (Tetrahydrofuran-3-yl)methanamine hydrochloride 17750392, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
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184950-35-4, (Tetrahydrofuran-3-yl)methanamine hydrochloride is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5- (2,3-difluorobenzyloxymethyl) isoxazole-3-carboxylic acid (0.54 g, 2.0 mmol), Tetrahydrofuran-3-ylmethylamine hydrochloride (0.41 g, 3.0 mmol), Triethylamine (0.30 g, 3.0 mmol) And 1 – hydroxybenzotriazole (0.03 g, 0.2 mmol) Was added to chloroform (amylen added product) (5 mL). To the mixture, 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (0.46 g, 2.4 mmol) was added at room temperature, After stirring overnight, And concentrated under reduced pressure. Dilute hydrochloric acid was added to the residue, And extracted three times with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, Washed with saturated brine, After drying with anhydrous sodium sulfate, Reduction It was concentrated under pressure. The residue was subjected to silica gel column chromatography, The following equation Indicated by N- (tetrahydrofuran-3-ylmethyl) -5- (2,3-difluorobenzyloxymethyl) isoxazole-3-carboxamide (Hereinafter referred to as the present amide compound (274)) 0.25 g was obtained.

184950-35-4, 184950-35-4 (Tetrahydrofuran-3-yl)methanamine hydrochloride 17750392, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; SUMITA, YUSUKE; (264 pag.)JP2015/51963; (2015); A;,
Tetrahydrofuran – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22929-52-8,Dihydrofuran-3(2H)-one,as a common compound, the synthetic route is as follows.

General procedure: Similar to as described in General Procedure Y Step 1, diethyl oxalate was reacted withoxolan-3-one to give 400 mg (5percent) of ethyl 2-oxo-2-(4-oxooxolan-3-yl)acetate as yellow oil..; Step 1: A solution of cycloalkylketone (1.0 eq.) in EtOH (0.5 mL/mmol) was cooled to 0 ¡ãC, then sodium ethoxide (21percent wt solution in EtOH, 1.1 eq.) was added. To this mixture was added diethyl oxylate (1.0 eq.) and the mixture was allowed to warm to room temperature overnight. In vacuo concentration provided the desired product of sufficient purity to be used directly (yield assumed to be quantitative)., 22929-52-8

The synthetic route of 22929-52-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.453-20-3,3-Hydroxytetrahydrofuran,as a common compound, the synthetic route is as follows.

In a 25L reaction flask,678 g (7.7 mol) of 3-hydroxy tetrahydrofuran was dissolved in 8 L of anhydrous dichloromethane,then add 1.13 L (14mo 1) anhydrous pyridine. The reaction solution was cooled to 0 C and a solution of acetyl chloride (600 ml, 8.4 mol 1) in dichloromethane (2 L) was slowly added along with stirring. After dripping up to 25 C for about two hours, continue to stir for 3 hours, After completion of the reaction, (10 L)water was added to the reaction solution, and the mixture was allowed to stand for half an hour. After complete delamination, the dichloromethane layer was collected , evaporated and dried under reduced pressure to give 910 g of tetrahydrofuranyl-3-acetate (racemic) , 91% yield as a colorless liquid.

453-20-3, 453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; Hangzhou Shukang Biological Co., Ltd.; Lin Lu; (10 pag.)CN106957287; (2017); A;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem