90319-52-1, (R)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
m-benzyloxy cinnamic acid (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¡ã 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¡ã 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: 93percent. 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)., 90319-52-1
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Reference£º
Patent; Zhang, Qiang; Zhang, Rongxia; Tian, Guanghui; Li, Jianfeng; Zhu, Fuqiang; Jiang, Xiangrui; Shen, Jingshan; US2014/46074; (2014); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem