反応 #1772021

反応方程式

EDCI

α-bromophenylacetic acid

(S)-(−)-1-phenylethanol

→

title compound

収率 73.0%

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

収率 73.0%

溶媒

ethyl acetate

dichloromethane

反応条件

後処理

1. 1
   洗浄washed (H2O×2, brine)
2. 2
   乾燥dried (Na2SO4)
3. 3
   ろ過filtered
4. 4
   濃縮concentrated
5. 5
   その他to give a pale yellow oil

実験手順

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).

出典