Tag: 123770-62-7

123770-62-7, Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Production Example 99 (0741) Ethyl 5-hydroxymethylisoxazole-3-carboxylate (1.71 g, 10.0 mmol), 2,2,2-trifluoroethylmethanesulfonate (5.34 g, 30 mmol), N,N-dimethylformamide (30 ml) and 60% sodium hydride (0.48 g, 12.0 mmol) were mixed at 0C, under a nitrogen atmosphere. The mixture was heated to room temperature and stirred for 16 hours, then added to a saturated aqueous ammonium chloride solution, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with water and 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 1.02 g of ethyl 5-(2,2,2-trifluoroethoxymethyl)isoxazole-3-carboxylate represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 1.41 (3H, t), 3.91(2H, q), 4.43(2H, q), 4.80(2H, s), 6.73(1H, s), 123770-62-7

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.123770-62-7,Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

Ethyl chlorooximidoacetate (10 g, 66 mmol) in CHCl3 (80 mL) is slowly added to propargyl alcohol (4.7 mL, 81 mmol) and K2CO3 (27 g, 198 mmol) in CHCl3 (80 mL). The addition is accompanied by an exothermic reaction which causes the chloroform to reflux. After being allowed to cool to RT, the mixture is stirred overnight. The reaction mixture is filtered and the residue is rinsed with chloroform and concentrated in vacuo. The crude product is purified by chromatohraphy (Biotage 40M, EtOAc/Hex:20/80) to yield 3.23 g (29% yield) of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate as an oil. 1H NMR (400 MHz, CDCl3) delta 6.69, 4.86, 4.45, 4.42. A solution of diethylaminosulfur trifluoride (DAST) (2.8 mL, 21 mmol) in 30 mL CH2Cl2 is added dropwise to a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (3.0 g, 18 mmol) in 30 mL CH2Cl2 at -78 C. The mixture is stirred at -78 C. for 1 h and then warmed to RT over 3 h. Water (10 mL) and 30 mL of 2.5% aqueous sodium bicarbonate solution are added successively and the organic layer is separated, dried (MgSO4) and evaporated in vacuo. The residue is purified by chromatography (Biotage 40M, EtOAc/Hex:20/80) to give 1.83 g (60% yield) of ethyl 5-(fluoromethyl)isoxazole-3-carboxylate as an oil. 1H NMR (400 MHz, CDCl3) delta 6.82, 5.54, 5.42, 4.47, 1.43. 10% Aqueous sodium hydroxide solution (5 mL) is added to a solution of ethyl 5-(fluoromethyl)isoxazole-3-carboxylate (1.82 g, 10 mmol) in ethanol (30 mL) at RT. The mixture is stirred for 2 h and the solvents are evaporated in vacuo. The residue is dissolved in water and acidified to pH 1 with 35% HCl. Ethanol is added, solvents are evaporated in vacuo and the residue is azeotroped with ethanol. Ethanol is added and the mixture filtered to remove inorganic solids. Evaporation in vacuo of the filtrate gives 0.95 g (63% yield) of 5-(fluoromethyl)isoxazole-3-carboxylic acid as a tan solid. 1H NMR (400 MHz, DMSO-d6) delta 7.05, 5.67, 5.56. Oxalyl chloride (0.85 mL, 9.8 mmol) is added dropwise to a suspension of 5-(fluoromethyl)isoxazole-3-carboxylic acid (0.94 g, 6.5 mmol) and a catalytic amount of DMF in 20 mL CH2Cl2. After 1 h, the volatiles are removed in vacuo and the remaining residue is dissolved in acetone. To this solution is added an aqueous solution of sodium azide (0.59 g, 9.1 mmol) at 0 C. with vigorous stirring. Volatiles are removed in vacuo and the residue washed with water and dried under nitrogen to yield 0.57 g (51% yield) of 5-(fluoromethyl)isoxazole-3-carbonyl azide as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 7.21, 5.71, 5.59. Example 605 is prepared according to Method F, making non-critical modifications. Yield 37%. HRMS (ESI) calcd for Cl3H13ClFN3O4+H 330.0657 found 330.0649

As the paragraph descriping shows that 123770-62-7 is playing an increasingly important role.

Reference£º
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

123770-62-7, Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Production Example 199 (0842) Ethyl 5-hydroxymethylisoxazole-3-carboxylate (0.29 g, 1.7 mmol) was dissolved in tetrahydrofuran (10 mL), and 3-fluoro-2-naphthylmethyl bromide (0.48 g, 2.0 mmol) and 18-crown-6 (0.05 g, 0.2 mmol) were added thereto. Sodium hydride (60% oil-based) (0.14 g, 3.4 mmol) was slowly added thereto at room temperature, and the mixture was stirred at room temperature overnight. Then, dilute hydrochloric acid was added thereto, and the mixture was extracted three times 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 dissolved in ethanol (4 mL), and an aqueous solution obtained by dissolving potassium hydroxide (0.56 g, 10 mmol) in water (2 mL) was added thereto at room temperature, and then the mixture was stirred at 80C for 3 hours. Water was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Tert-butyl methyl ether was added to the concentrate, and the aqueous layer was fractionated. Dilute hydrochloric acid was added to the resulting aqueous layer, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 0.48 g of 5-(3-fluoro-2-naphthylmethoxymethyl)isoxazole-3-carboxylic acid represented by the following formula. The product was subjected to a next reaction without purification

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various.

Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem