Day: November 18, 2020

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.

A suspension of magnesium bromide (2 eq/mole, 108.17 g) in acetonitrile (300 ml) is added, at 0C, with acetic anhydride (4 eq/mole, 119.95 g). The mixture is left under stirring for 15 minutes at 0C, then 3-hydroxymethyl tetrahydrofuran (30 g, 293 mmoles) is added. The mixture is kept at the reflux temperature until complete disappearance of the substrate (18 h), then is added with 300 ml of a sodium bicarbonate saturated solution and left under stirring at room temperature for 30 minutes. The mixture is extracted with ethyl acetate (3×100 ml), the organic phase is dried over anhydrous sodium sulfate, filtered and the solvent is evaporated off to a residue. The reaction conversion is quantitative. 59.02 g (yield: 75%) of a colourless oil are obtained. The gas-chromatographic and nuclear magnetic resonance analysis of the residue show the presence of a mixture consisting of 2-acetoxymethyl-4-bromo-butyl-1-acetate and its 2-bromomethyl-4-acetoxybutyl-1-acetate isomer in a yield of 90% (53.12 g) and 10% (5.902 g), respectively. This mixture can be used directly in the subsequent reaction for the alkylation of 2-aminochloropurine (IV) as no addition products due to the presence of the minor isomer are formed. (The two isomers can anyway be separated, if necessary, by fractional distillation).2-Acetoxymethyl-4-bromo-butyl-1-acetate:1H-NMR (d, ppm): 1.83 (q, 2H, CH2) 1.98 (s, 6H, 2(CH3)) 2.07-2.13 (m, 1H, CH) 3.45 (t, 2H, CH2Br) 4.04 (d, 4H, 2(CH2O)).13C-NMR (d, ppm): 21.33 (CH2Br) 31.03(2(CH3)) 32.01 (CH2) 36.55 (CH) 64.00 (2(CH20)) 171.37 (2(CO)).2-Bromomethyl-4-acetoxy-butyl-1-acetate:1H-NMR (d, ppm): 1.63 (m, 2H, CH2) 1.88 (s, 3H, CH3) 1.90 (s, 3H, CH3) 1.99 (m, 1H, CH) 3.37 (d, 2H, CH2Br) 4.01 (d, 2H, CH2O) 4.13 (t, 2H, CH2O).13C-NMR (d, ppm): 20.55 (CH3) 21.03 (CH3) 28.37 (CH) 34.49 (CH2Br) 36.03 (CH2) 61.25 (OCH2) 66.26 (OCH2) 170.39 (CO) 170.42 (CO).

124391-75-9, 124391-75-9 (S)-(Tetrahydrofuran-3-yl)methanol 40784875, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; RECORDATI S.A.; WO2004/7418; (2004); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

88675-24-5, Tetrahydrofuran-3-amine is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

88675-24-5, Step-a: Synthesis of 3-Nitro-N-(tetrahydrofuran-3-yl)benzamide Tetrahydrofuran-3-amine (0.1 g, 1.148 mmol) and 3-nitrobenzoic acid (0.192 g, 1.148 mmol) were taken in pyridine (2 ml), to the mixture EDC.HCl (0.220 g, 1.148 mmol) was added, the reaction mixture was stirred under nitrogen for 10 hrs at room temperature. The reaction mixture was diluted with cold water (15 ml), extracted with ethyl acetate (2*10 ml). Combined organic layer was washed with satd. aq. sod bicarbonate and dil HCl, the organic layer was dried over sodium sulfate and concentrated under vacuum to afford the title product (240 mg). 1HNMR (400 MHz, CDCl3): delta 8.62-8.61 (m, 1H), 8.39-8.36 (m, 1H), 8.19-8.17 (m, 1H), 7.67 (t, 1H, J=8 Hz), 6.62 (d, 1H, J=6 Hz), 4.79-4.75 (m, 1H), 4.08-4.00 (m, 1H), 3.93-3.83 (m, 3H), 2.44-2.37 (m, 1H), 2.01-1.98 (m, 1H).

As the paragraph descriping shows that 88675-24-5 is playing an increasingly important role.

Reference£º
Patent; Dave, Bhavesh; Banerjee, Rakesh Kumar; Phukan, Samiron; Khoje, Abhijit Datta; Hangarge, Rajkumar; Jadhav, Jitendra Sambhaji; Palle, Venkata P.; Kamboj, Rajender Kumar; US2015/133424; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

124391-75-9, (S)-(Tetrahydrofuran-3-yl)methanol is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 85B (tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate To a solution of (tetrahydrofuran-3-yl)methanol (5.15 g, 50.4 mmol) in dichloromethane (200 mL) were added triethylamine (21.08 mL, 151 mmol) and p-toluenesulfonyl chloride (9.61 g, 50.4 mmol) and the mixture was stirred at room temperature overnight. The reaction mixture was washed with water (100 mL) and brine (100 mL). The organic layer was dried with sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography using an Analogix Intelliflash280 (SiO2, 0-40% ethyl acetate in hexane) to provide the title compound (12.5 g, 97%) as colorless viscous liquid. 1H NMR (300 MHz, DMSO-D6) delta ppm 1.40-1.51 (m, 1H) 1.83-1.95 (m, 1H) 2.43 (s, 3H) 3.28-3.31 (m, 1H) 3.31-3.37 (m, 1H) 3.51-3.67 (m, 3H) 3.90-4.00 (m, 2H) 7.48-7.51 (m, 2H) 7.78-7.82 (m, 2H); MS (DCI/NH3) m/z 274 (M+NH4)+.

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

Reference£º
Patent; ABBOTT LABORATORIES; US2009/105306; (2009); 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

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;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

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;,
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.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;,
Tetrahydrofuran – Wikipedia
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;,
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

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;,
Tetrahydrofuran – Wikipedia
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 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;,
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 – [(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;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem