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, Example 338E (100 mg, 0.20 mmol), (tetrahydro-furan-3-yl) -methanol (82 mg, 0.80 mmol), DBAD (92 mg, 0.40 mmol), PPh-polymer supported (133 mg, 0.40 mmol) and THF (5 mL) were mixed, and shaken overnight. The mixture was filtered. The filtrate was concentrated. To the residue was added methanol (8.0 mL) and 4N HCL in dioxane (0.50 mL). The mixture was stirred at room temperature for 8 hours. All the solvents were removed. The residue was washed with ethyl acetate (10 mLx2), and dried to give the desired product (48 mg, 67%).

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

Reference£º
Patent; ABBOTT LABORATORIES; WO2004/80973; (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.184950-35-4,(Tetrahydrofuran-3-yl)methanamine hydrochloride,as a common compound, the synthetic route is as follows.

Production Example 249 (0570) 5-(1-Fluoro-2-naphthylmethoxymethyl)isoxazole-3-carbo xylic acid (0.59 g, 1.5 mmol), tetrahydrofuran-3-ylmethylamine hydrochloride (0.83 g, 6.0 mmol), triethylamine (0.61 g, 6.0 mmol) and 1-hydroxybenzotriazole (0.06 g, 0.4 mmol) were added to a mixed solvent of chloroform (amylene addition product) (4 mL) and tetrahydrofuran (4 mL). 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (0.92 g, 4.8 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 0.07 g of N-(tetrahydrofuran-3-ylmethyl)-5-(1-fluoro-2-naphthylmethox ymethyl)isoxazole-3-carboxamide (hereinafter, referred to as Compound of Present Invention (258)) represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 1.60-1.73 (1H, m), 2.03-2.14 (1H, m), 2.52-2.63 (1H, m), 3.46 (2H, t), 3.59 (1H, dd), 3.73-3.80 (1H, m), 3.83-3.95(2H, m), 4.69(2H, s), 4.86(2H, s), 6.76 (1H, s), 6.93 (1H, br s), 7.40-7.52 (1H, m), 7.52-7.59(2H, m), 7.66(1H, d), 7.81-7.88 (1H, m), 8.07-8.14 (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

86087-23-2, (S)-(+)-3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Take 4-bromo-2-(4-fluorobenzyl)chlorobenzene 148kg,(S)-3-hydroxytetrahydrofuran (45kg) dissolved in 300kg tetrahydrofuranThe ice bath was cooled to 0C and under the protection of nitrogen, a solution of potassium tert-butoxide in tetrahydrofuran was added dropwise.(tert-butanol potassium 56kg, tetrahydrofuran 150kg) 30min drop, drop is completed,5-10 C reaction 1h, after the end of the reaction, add 300kg of water to quench the reaction,Tetrahydrofuran was recovered by distillation and the residue was extracted with 300 kg of ethyl acetate and dried over anhydrous sodium sulfate.After filtration, the solvent was recovered from the filtrate and recrystallized from 70% ethanol to obtain 161 kg of a white solid with a yield of 88%., 86087-23-2

The synthetic route of 86087-23-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Jiangsu Engineering Polytechnic College; Feng Chengliang; Yan Bin; (12 pag.)CN107652278; (2018); A;,
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

a) 2,2-Dimethyl-4-oxo-4-piperidin-l-yl-butyric acid; To solution of 2,2-dimethylsuccinic anhydride (1.0 g, 7.8 mmol) and triethylamine (0.79 g, 078 mmol) in CH2Cl2 (40 mL) was slowly added a solution of piperidine (0.66 g, 7.8 mmol) in CH2Cl2 (10 mL) at RT. The mixture was stirred for 4 hrs. NaOH 1.0M solution was added and the aqueous layer collected and subsequently acidified to pH 4 using HCl 2.0 M solution. Extraction with CHCI3 and evaporation of the solvent gave a crude product clean enough to be used without further purification.1.63 g; 98percentC11H19NO3 calculated 213; found M+ 214/M- 212Lc Rt (5 min)= 1.56 NMR (400 MHz, dmso-d6): 1.10 (6H, s); 1.32-1.37 (2H, m); 1.40- 1.44(2H, m); 1.50- 1.55 (2H, m); 2.50 (2H, s); 3.31-3.35 (4H, m); 11.7 (IH, br s)., 17347-61-4

The synthetic route of 17347-61-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SIENA BIOTECH S.P.A.; WYETH PHARMACEUTICALS; WO2007/98826; (2007); A2;,
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

Example 22; 1- (4-{(2S)-3-[(6-Chloronaphthalen-2-yl)sulfonyl]-2- hydroxypropanoyl} piperazin-1-yl)-3-methylpyrrolidin-2-one; 22a) 1-(4-Benzylpiperazin-1-yl)-3-methylpyrrolidin-2-one; A mixture of 3-methyldihydrofuran-2 (3H)-one g), thionyl chloride (1.5 ml) and zinc chloride (10 mg) was stirred at 80C for 15 hours. The mixture was cooled to room temperature, and the reaction mixture was added dropwise to a solution of 4-benzylpiperazin-1-amine (3.8 g) in THF (50 mL) at 0C, followed by stirring at 0C for 2 hours. Sodium hydride (60% in oil; 2.4 g) was added thereto and the mixture was stirred at room temperature for 15 hours. Ice was. added thereto, and then the reaction mixture was concentrated under reduced pressure. The residue was diluted with water, and extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by basic silica gel column chromatography (ethyl acetate/hexane = 1/5) to obtain the title compound (2.0 g, 37%) as a yellow oil. NMR (CDC13) 5: 1.18 (3H, d, J = 7.2), 1.48-1.63 (lH, m), 2.12-2.29 (lH, m), 2.28-2.49 (lH, m), 2.62 (4H, dd), 2.84- 3.08 (4H, m), 3.26-3.47 (2H, m), 3.48-3.64 (2H, m), 7.20- 7.40 (5H, m).

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

Reference£º
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/113504; (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.97-99-4,(Tetrahydrofuran-2-yl)methanol,as a common compound, the synthetic route is as follows.

A solution of 7-hydroxy-2-(4-(1-methyl-1H-pyrazol-4-yl)benzyl)isoindolin-1-one (0.10 g) obtained in Reference Example 6, (R)-(tetrahydrofuran-2-yl)methanol (0.064 g) and tributylphosphine (0.13 g) in THF (4 mL) was added diazene-1,2-diylbis(piperidin-1-ylmethanone) (0.16 g) at 60C, and the mixture was stirred under a nitrogen atmosphere at 70C for 1 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated brine. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated. The residue was crudely purified by NH silica gel chromatography (hexane-ethyl acetate), and purified by HPLC (L-column2 ODS, mobile phase: water/acetonitrile (containing 0.1% NH4HCO3)) to give the title compound (0.035 g). MS: [M+H]+ 404.2 1H NMR (300 MHz, DMSO-d6) delta 1.73-1.91 (2H, m), 1.92-2.13 (2H, m), 3.62-3.74 (1H, m), 3.79-3.92 (4H, m), 3.99-4.14 (2H, m), 4.15-4.31 (3H, m), 4.63 (2H, s), 6.97-7.11 (2H, m), 7.24 (2H, d, J = 8.1 Hz), 7.42-7.58 (3H, m), 7.82 (1H, d, J = 0.8 Hz), 8.10 (1H, s)., 97-99-4

The synthetic route of 97-99-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

10374-51-3, 5-(Hydroxymethyl)dihydrofuran-2(3H)-one is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,10374-51-3

A stirrer, a thermometer,Into a 50 mL reactor equipped with a gas inlet tube,1.8 g (0.0155 mol) of gamma-hydroxymethyl-gamma-butyrolactone, 1.4 g(0.0171 mol) of pyridine,5.6 g of toluene was charged, 4.9 g (0.0166 mol) of stearoyl chloride was dropped into a nitrogen atmosphere, and the reaction was carried out at 25 C. for 2 hours.The obtained reaction solution was washed with water, washed with an acid, deacidified and washed with water, and the toluene layer was concentrated to obtain 4.3 g of the desired compound as a solid.The solid obtained was a white solid (Infrared absorption spectrum (KBr tablet method): 2924, 2855, 1775, 1731, 1153 cm -1). The structure of the compound was confirmed by 1 H-NMR spectrum and it was confirmed to be a compound represented by the following structural formula (Attribution number of 1 H-NMR spectrum in the formula, and its assignment is shown in Table 1 ).

As the paragraph descriping shows that 10374-51-3 is playing an increasingly important role.

Reference£º
Patent; NIPPON FINE CHEMICAL CO LTD; HASHIMOTO, AKIHIRO; KODERA, HIROKI; KATSUMATA, YUKI; SHAKUSHI, RISA; OHASHI, YUKIHIRO; (42 pag.)JP6039336; (2016); B2;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

21461-84-7, (S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic Acid is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

70.0 g (0.538 mol) of compound 1A is dissolved in 315 ml of CH2Cl2. The solution is cooled and kept at 3C under N2 atmosphere. 170.7 g (1.345 mol) of oxalyl chloride is slowly added afterwards 0.80 ml of DMF is carefully added to the solution. After completion of the addition, the mixture is warmed to room temperature and stirred for 2h. Then, the solvent is evaporated under reduced pressure. The remaining material is dissolved in 15 ml of CH2Cl2 and the solvent is evaporated once again. 69.2 g (0.646 mol) of 2,6-lutidine and 79.8 g (1.076 mol) of t-BuOH are dissolved in 350 ml of CH2Cl2. The mixture is cooled to 3C. Then a solution of acyl chloride previously synthesized in 50 ml of CH2Cl2 is added dropwise over a period of 10 min. At the end of the addition, the mixture is warmed to room temperature and stirred for 12 h. Solvent is evaporated. The remaining oil is dissolved in 500 ml of ethyl acetate and purified on Silica plug (around 2L of ethyl acetate). The solution is concentrated and treated with charcoal during 30 min. After filtration on celite, the solvent is evaporated under reduced pressure to obtain a yellow solution which is kept for recrystallization to obtain compound 2A as pale yellow powder., 21461-84-7

Big data shows that 21461-84-7 is playing an increasingly important role.

Reference£º
Patent; OctreoPharm Schiences GmbH; Chematech; Boschetti, Frederic, Dr.; Bouterfa, Hakim, Dr.; Kaufmann, Jens, Dr.; (18 pag.)EP3015462; (2016); 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

A stirring solution of compound 17-1 (112 mg, 0.232 mmol), DMAP (28 mg, 0.232 mmol) and 2,2-dimethylsuccinic anhydride (89 mg, 0.695 mmol) in dry pyridine (4 mL) is heated for 4 hours at 120¡ãC. Another 90 mg (0.7 mmol) of anhydride is added and heating is continued overnight. The mixture is concentrated to dryness and the residue is diluted in ethyl acetate, washed twice with HCl 1 N, water and brine, dried over sodium sulfate and concentrated to dryness. The residue is purified by flash chromatography on silica gel (ethyl acetate/hexanes 10percent to 30percent) to yield the title compound 14-1 as a white solid (87 mg, 61percent).1H NMR (400 MHz, DMSOd6): delta [ppm] 12.16 (s, 1 H), 6.33 (s, 1 H), 4.64 (d, 1 H), 4.54 (s, 1 H), 4.35 (d x d, 1 H), 3.47 (s, 3H), 2.73 (m, 1 H), 2.53 (d, 1 H), 2.45 (d, 1 H), 2.42 (m, 1 H), 2.15 (m, 1 H), 1.92 (m, 1 H), 1.75 (m, 1 H), 1.70-0.90 (m, 20H), 1.62 (s, 3H), 1.15 (s, 3H), 1.14 (s, 3H), 0.95 (s, 3H), 0.91 (s, 3H), 0.89 (s, 3H), 0.84 (s, 3H), 0.80 (s, 3H). LC/MS: m/z = 614.72 (M+H+). HPLC (Method A): tR = 31.62 min., 17347-61-4

The synthetic route of 17347-61-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VIROCHEM PHARMA INC.; WO2009/100532; (2009); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

915095-89-5, (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add 36.6g of compound of Formula 5, 350ml of dioxane, 38g of bis(pinacolato)diboron(formula 6), 30g of potassium acetate, 1.47g of dppfPdCl, and heat up the oil bath to 100 with nitrogen filling. The reaction was carried out at a temperature of 8 C for 8 hours. After the reaction, the temperature was lowered to room temperature, filtered, and the filtrate was washed with water and concentrated to obtain a yellow solid, which was refined by adding ethanol to obtain a white solid (Formula 7), 26.1 g. The yield was 71.3%. HPLC: 98.6%., 915095-89-5

915095-89-5 (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran 15941217, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; Huanggang Luban Pharmaceutical Co., Ltd.; Yang Xiaolong; Pei Pibing; Zhang Jianjun; Yang Tiebo; Chen Qian; (22 pag.)CN110698467; (2020); A;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem