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With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 4h;Inert atmosphere; Large scale reaction; |
To a stirred solution of 4 (2 kg, 8 mol) in CH2Cl2 (2 L) was added oxalyl chloride (1.4 L, 16 mol) dropwise at 0 C. The resulting solution was stirred at room temperature for another 4 h and concentrated in vacuo. To a stirred solution of (R)-4-phenyloxazolidin-2-one (1.3 kg, 8 mol) and TEA (1.7 L, 12 mol) in CH2Cl2 (4.8 L) at 0 C was added the substituted cinnamic chloride in CH2Cl2 (800 mL) dropwise. The mixture was stirred at 0 C for 1 h and then raised to room temperature for 3 h when a saturated solution of NH4Cl (600 mL) was added. The aqueous layer was separated, and the organic solution was washed with water (600 mL × 3), brine (800 mL), and dried over Na2SO4. The organic solution was evaporated and 2.9 kg of 5 was obtained after recrystallization in EtOH in 93% yield |
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With thionyl chloride; for 1h;Reflux; |
(R,E)-3- (3- (3-benzyloxy) phenyl) acryloyl)-4- phenyl oxazolidin-2-one <strong>[122024-75-3]m-benzyloxy cinnamic acid</strong> (9.0g, 35.4mmol) was dissolved in thionyl chloride (25ml) and refluxed for 1 hour, and the mixture was concentrated to remove thionyl chloride for further use. 4R-phenyl-2-oxazolidinone (5.6g, 34.4mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran (25ml) was added and when it was cooled to -78C, n-butyl lithium (1.6M, 22ml, 35.4mmol) was added dropwise, and the reaction was carried out for 30 minutes. Then the solution (35ml) of m-benzyloxy cinnamoyl chloride in tetrahydrofuran as prepared above was added dropwise and the reaction was continued for 30 minutes. After that, it was slowly raised to 0C, the reaction was continued for 2 hours, then it was quenched with saturated ammonium chloride solution. The resulted mixture was then concentrated to remove tetrahydrofuran and extracted with ethyl acetate for three times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and recrystallized with petroleum ether and ethyl acetate to give a white solid 14g, yield: 93%. 1HNMR(300MHz, CDCl3): delta 7.9(1H, d, J=15.5), 7.7(1H, d, J=15.3), 7.3-7.5(11H, m), 7.2 (2H, m), 7.0(1H, dd, J=2.3, 8.6), 5.6(1H, dd, J=4.0,9.0), 5.1(2H, s), 4.8 (1H, t, J=8.9, 17.7), 4.3(1H, dd, J=3.9, 8.8). ESI-MS: 422.2 (M+Na). |
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With thionyl chloride; for 1h;Reflux; |
Example 1 (R,E)-3-(3-(3-benzyloxy)phenyl)acryloyl)-4-phenyl oxazolidin-2-one <strong>[122024-75-3]m-benzyloxy cinnamic acid</strong> (9.0 g, 35.4 mmol) was dissolved in thionyl chloride (25 ml) and refluxed for 1 hour, and the mixture was concentrated to remove thionyl chloride for further use. 4R-phenyl-2-oxazolidinone (5.6 g, 34.4 mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran (25 ml) was added and when it was cooled to -78 C., n-butyl lithium (1.6M, 22 ml, 35.4 mmol) was added dropwise, and the reaction was carried out for 30 minutes. Then the solution (35 ml) of m-benzyloxy cinnamoyl chloride in tetrahydrofuran as prepared above was added dropwise and the reaction was continued for 30 minutes. After that, it was slowly raised to 0 C., the reaction was continued for 2 hours, then it was quenched with saturated ammonium chloride solution. The resulted mixture was then concentrated to remove tetrahydrofuran and extracted with ethyl acetate for three times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and recrystallized with petroleum ether and ethyl acetate to give a white solid 14 g, yield: 93%. 1HNMR (300 MHz, CDCl3): delta 7.9 (1H, d, J=15.5), 7.7 (1H, d, J=15.3), 7.3-7.5 (11H, m), 7.2 (2H, m), 7.0 (1H, dd, J=2.3, 8.6), 5.6 (1H, dd, J=4.0, 9.0), 5.1 (2H, s), 4.8 (1H, t, J=8.9, 17.7), 4.3 (1H, dd, J=3.9, 8.8). ESI-MS: 422.2 (M+Na). |
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