Day: September 29, 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.53662-85-4,Methyl tetrahydrofuran-3-carboxylate,as a common compound, the synthetic route is as follows.,53662-85-4

Example 11A methyl 3-bromotetrahydrofuran-3-carboxylate 5.0 g (38.419 mmol) of methyl tetrahydrofuran-3-carboxylate (prepared analogously to: J. Org. Chem. 1996, 2690) were dissolved in 200 ml of THF and cooled to -78 C., and then 76.83 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF were added. After 30 min at -78 C., 10.26 g (57.63 mmol) of N-bromosuccinimide suspended in 50 ml of THF were added gradually. Thereafter, the mixture was left to warm up to RT overnight. The mixture was then admixed with water and extracted with ethyl acetate. The phases were separated and the aqueous phase was extracted twice more with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution and then dried over sodium sulfate, filtered and concentrated. The crude product was purified by means of chromatography on silica gel (eluent: dichloromethane). This gave 491 mg (6% of theory) of the target compound. 1H NMR (400 MHz, CDCl3): delta [ppm]=2.49 (ddd, 1H), 2.74 (ddd, 1H), 3.83 (s, 3H), 4.03-4.10 (m, 1H), 4.11-4.17 (m, 2H), 4.31 (d, 1H).

The synthetic route of 53662-85-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Ackerstaff, Jens; Griebenow, Nils; Knorr, Andreas; Wunder, Frank; Li, Volkhart Min-Jian; US2013/172372; (2013); 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

To alpha-methyl-gamma-butyrolactone (130 g, 1.3 mol) was added phosphoroustribromide (101 mL, 1.13 mol) and this was then heated at reflux for 8 hours. The reaction was slowly poured onto iced water (500 mL). Dichloromethane (500 mL) was added and this was stirred overnight at ambient temperature. The layers were separated, dried over magnesium sulphate, filtered, and evaporated to dryness. The resultant yellow oil was passed through a pad of silica (3:1 hexane:ethyl acetate). This gave 18 (158.5 g, 67%) as an oil., 1679-47-6

The synthetic route of 1679-47-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wainwright, Philip; Maddaford, Adrian; Zhang, Xiurong; Billington, Helen; Leese, David; Glen, Rebecca; Pryde, David C.; Middleton, Donald S.; Stephenson, Peter T.; Sutton, Scott; Nucleosides, nucleotides and nucleic acids; vol. 32; 9; (2013); p. 477 – 492;,
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.118399-28-3,(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate,as a common compound, the synthetic route is as follows.

4. Synthesis of intermediate 5a (0359) Exact Mass: 391.25 (0360) (0361) 5a [00127] To the solution of intermediate 4 (4.8 g, 20.4 mmol) in THF (80 mL) was added a (3.2 g, 20.4 mmol), and the solution was stirred at room temperature overnight. After completion of the reaction, the solvent was removed in vacuo to afford intermediate 5a (7.2 g, 100%) as yellow oil, which was used in the next reaction without any further purification., 118399-28-3

As the paragraph descriping shows that 118399-28-3 is playing an increasingly important role.

Reference£º
Patent; MERRIMACK PHARMACEUTICALS, INC.; DRUMMOND, Daryl, C.; GENG, Bolin; KIRPOTIN, Dmitri, B.; TIPPARAJU, Suresh, K.; KOSHKARYEV, Alexander; (125 pag.)WO2017/123616; (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.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

Production Example 242 (0563) 5-[3-(3-Fluorophenyl)propyl]isoxazole-3-carboxylic acid (0.25 g, 1.0 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.21 g, 1.5 mmol), triethylamine (0.15 g, 1.5 mmol) and 1-hydroxybenzotriazole (0.01 g, 0.1 mmol) were added to chloroform (amylene addition product) (2.5 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.23 g, 1.2 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 0.22 g of N-(tetrahydrofuran-3-ylmethyl)-5-[3-(3-fluorophenyl)propyl] isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (251)) represented by the following formula. 1H-NMR(CDCl3, TMS, delta(ppm)):1.63-1.73(1H, m), 2.00-2.13(3H, m), 2.52-2.62(1H, m), 2.69(2H, t), 2.81(2H, t), 3.46(2H, t), 3.59(1H, dd), 3.73-3.80(1H, m), 3.83-3.95(2H, m), 6.46(1H, s), 6.85-6.98(4H, m), 7.22-7.29 (1H, m), 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; 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.4100-80-5,3-Methyldihydrofuran-2,5-dione,as a common compound, the synthetic route is as follows.

Add methylsuccinic anhydride (5g, 43.8 mmole) to a stirred suspension of 1,3- difluorobenzene (25g, 219.1 mmole) and aluminum chloride (11.7g, 87.6 mmole), keeping the temperature less than 50¡ãC. Stir the reaction overnight at 50¡ãC and then for 3 days at 78¡ãC. Cool to room temperature and slowly add reaction mixture to a mixture of 3N HCI (40 mL) and ice (40g). Add methylene chloride (80 mL) and separate the organic layer, then extract the aqueous phase with additional methylene chloride (70 mL). Wash the combined organic phase twice with 1 N NaOH solution (80 mL) and then acidify the combined basic wash with 6N HCI. Extract the acidic aqueous phase twice with methylene chloride (100 mL), dry over Na2SO4 and concentrate to obtain product. ESMS 229, tR (min) = 1.57. 1H-NMRshowed a 4: 1 mixture of isomeric products.

4100-80-5, 4100-80-5 3-Methyldihydrofuran-2,5-dione 20051, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; AVENTIS PHARMACEUTICALS INC.; WO2005/111025; (2005); 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.138498-97-2,2-(Tetrahydrofuran-3-yl)acetic acid,as a common compound, the synthetic route is as follows.

To a stirred solution of ethyl 1 -(6-(3, 5-difluoro-2-((2-methyl-4-(piperidin-4- yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate (500 mg, 0.910 mmol) in DMF (7 mL) stirred at 0C, were added 2-(tetrahydrofuran-3-yl)acetic acid (142 mg, 1.092 mmol) and BOP-CI (347 mg, 1.365 mmol). The reaction mixture was stirred at 0C for 30 minutes and then DIPEA (0.477 mL, 2.73 mmol) was added dropwise. The reaction mixture was stirred at 25 C for 12 hours and then was partitioned between water (10 ml) and EtOAc (20 ml). The organic phase was separated and the aqueous phase was further extracted with EtOAc (2×30 ml). The combined organic phase was washed with water (2×20 ml), dried over anhydrous Na2SO4 and then concentrated under reduced pressure. The crude product was purified by column chromatography (using 100-200 mesh silica gel, initially eluted with EtOAc/Hexane 10/90 to 20/80 to removed non-polar impurities, then with EtOAc/Hexane 8/2). The pure fractions were collected and concentrated under reduced pressure to afford the title compound (400 mg, 49.8 % yield) as a gummy solid.LCMS (a): Rt = 3.01 mi M/z = 662.34 (M+H)

138498-97-2, The synthetic route of 138498-97-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BOUILLOT, Anne Marie Jeanne; DODIC, Nerina; (120 pag.)WO2016/42536; (2016); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

453-20-3,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.

General procedure: To the mixture of 60% NaH (7.68 g, 0.053 mol), anhydrous THF (400 mL), (S)-tetrahydrofuran-3-ol (8.45 g, 0.096 mol) was added drop-wise at room temperature. The mixture was stirred at room temperature for 1 h a solution of compound 4a (10.0 g, 0.032 mol) in anhydrous THF (200 mL) was added via a dropping funnel over 1 h (the dropping funnel was rinsed with 15 mL of THF) at room temperature and the reaction mixture was stirred at room temperature for 2 h, the reaction was monitored by TLC. Then the solution was concentrated under a reduced pressure and the residue was poured into water with stirring, yielding a precipitate, then the mixture was filtered and washed with ice-water and ethanol, dried to afford compound 5b as yellow solid (9.8 g, 81.0%).

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

Reference£º
Article; OuYang, Yiqiang; Zou, Wensheng; Peng, Liang; Yang, Zunhua; Tang, Qidong; Chen, Mengzi; Jia, Shuang; Zhang, Hong; Lan, Zhou; Zheng, Pengwu; Zhu, Wufu; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 29 – 43;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

118399-28-3, (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of intermediate d (27g,115mmol) and morpholine (2Og, 230 mmol) in 200 mL of dioxane was stirred at 70 0C for 18 hours and concentrated, EtOAc (500ml) was added and washed with brine, dried over Na2SO4 and concentrated to afford the product e as an oil, which was used for the next step without further purification (3 Ig, 84%). MS (ESI) m/e (M+H+):323; 1H-NMR (CDCl3, 400 MHz): delta 7.38-7.31 (m, 5H), 5.85 (m, IH), 5.12 (br s, 2H), 3.92 (m, IH), 3.71-3.49 (m, 10H), 2.91 (m, IH), 2.50 (m, IH).

118399-28-3, 118399-28-3 (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate 697924, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; GENENTECH, INC.; WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; WO2008/61208; (2008); A2;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

16874-34-3, Ethyl tetrahydrofuran-2-carboxylate is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A flask was charged with 13.6 g of magnesium and 300 ml of tetrahydrofuran, to which 60.3 g of 1,4-dibromobutane was added dropwise at 50 C. After the completion of dropwise addition, the solution was stirred at 60 C. for one hour.To the solution below 40 C., 31.0 g of ethyl tetrahydrofurancarboxylate was added dropwise.The solution was stirred at room temperature for one hour, after which an aqueous solution of ammonium chloride was added for hydrolysis.Ordinary post-treatment yielded 30.2 g of 1-(2-tetrahydrofuranyl)cyclopentanol. In 80 ml of toluene were dissolved 16.8 g of 1-(2-tetrahydrofuranyl)cyclopentanol, 13.1 g of triethylamine, and 0.5 g of 4-(N,N-dimethylamino)pyridine. Then 10.7 g of acrylic chloride was added to the solution at 50 C., which was stirred at the temperature for one hour. Water, 50 ml, was added to the solution below 30 C., followed by ordinary post-treatment. Vacuum distillation yielded 18.1 g of 1-(2-tetrahydrofuranyl)cyclopentyl acrylate. The two-step yield was 80%. [0583] boiling point: 84-86 C./86 Pa [0584] IR (thin film): nu=2954, 2871, 1720, 1635, 1619, 1450, 1402, 1298, 1207, 1170, 1074, 1049, 983, 811 cm-1 [0585] 1H-NMR (300 MHz in CDCl3): delta=1.49-2.25 (12H, m), 3.70-3.92 (2H, m), 4.57 (1H, t), 5.72 (1H, dd), 6.04 (1H, dd), 6.29 (1H, dd) ppm, 16874-34-3

The synthetic route of 16874-34-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hasegawa, Koji; Kinsho, Takeshi; Watanabe, Takeru; US2004/68124; (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.57595-23-0,Methyl 4-oxotetrahydrofuran-3-carboxylate,as a common compound, the synthetic route is as follows.

57595-23-0, To a solution of DIEA (860 mI_, 4.99 mmol) in dry DCM (20 ml_) cooled to -78C under Argon was added a solution of methyl 4-oxotetrahydrofuran-3- carboxylate (628 mg, 4.63 mmol in 20 ml_ DCM) dropwise. The reaction mixture was stirred -78C for 30 minutes post addition and then treated dropwise with neat trifluoromethanesulfonic anhydride (820 mI_, 4.98 mmol). After stirring the reaction mixture for 2 h 0C, the reaction mixture was quenched by the cautious addition of cold water (11 ml_). The reaction mixture was warmed to ambient temperature and diluted with water and diethyl ether. The aqueous layer was extracted with diethyl ether and the combined organic layers washed with sat. NaHCC>3 and brine, then dried over MgS04. The resulting residue was concentrated in vacuo followed by flash chromatography (Si02, 0-50% DCM/heptane) to yield a pale yellow oil.

The synthetic route of 57595-23-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; LANTER, James C.; WALL, Mark; SUI, Zhihua; (0 pag.)WO2019/171278; (2019); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem