反应 #1772021

反应方程式

EDCI

α-bromophenylacetic acid

(S)-(−)-1-phenylethanol

→

title compound

收率 73.0%

(S)-1-Phenylethyl 2-bromo-2-phenylacetate

收率 73.0%

溶剂

ethyl acetate

dichloromethane

反应条件

后处理

1. 1
   洗涤washed (H2O×2, brine)
2. 2
   干燥dried (Na2SO4)
3. 3
   过滤filtered
4. 4
   浓缩concentrated
5. 5
   其他to give a pale yellow oil

实验过程

To a mixture of α-bromophenylacetic acid (10.75 g, 0.050 mol), (S)-(−)-1-phenylethanol (7.94 g, 0.065 mol) and DMAP (0.61 g, 5.0 mmol) in dry dichloromethane (100 mL) was added solid EDCI (12.46 g, 0.065 mol) all at once. The resulting solution was stirred at room temperature under Ar for 18 hours and then it was diluted with ethyl acetate, washed (H2O×2, brine), dried (Na2SO4), filtered, and concentrated to give a pale yellow oil. Flash chromatography (SiO2/hexane-ethyl acetate, 4:1) of this oil provided the title compound (11.64 g, 73%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.53-7.17 (m, 10H), 5.95 (q, J=6.6 Hz, 0.5H), 5.94 (q, J=6.6 Hz, 0.5H), 5.41 (s, 0.5H), 5.39 (s, 0.5H), 1.58 (d, J=6.6 Hz, 1.5H), 1.51 (d, J=6.6 Hz, 1.5H).

来源