반응 #46637

반응 방정식

EDCI

α-bromophenylacetic acid

(S)-(−)-1-phenylethanol

→

title compound

수율 73.0%

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

수율 73.0%

용매

ethyl acetate

dichloromethane

반응 조건

후처리

1. 1
   세척washed (H2O×2, brine)
2. 2
   건조dried (Na2SO4)
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타to give a pale yellow oil

실험 절차

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).

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