반응 #1772024

반응 방정식

2-fluorophenylacetic acid

(S)-1-phenylethanol

EDCI

→

title compound

수율 92.0%

(S)-1-Phenylethyl 2-(2-fluorophenyl)acetate

수율 92.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   농축The solvent was then concentrated
2. 2
   기타the residue partitioned with H2O-ethyl acetate
3. 3
   기타The phases were separated
4. 4
   추출the aqueous layer back-extracted with ethyl acetate (2×)
5. 5
   세척The combined organic phases were washed (H2O, brine)
6. 6
   건조dried (Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The residue was purified by silica gel chromatography (Biotage/0-20% ethyl acetate-hexane)

실험 절차

A mixture of 2-fluorophenylacetic acid (5.45 g, 35.4 mmol), (S)-1-phenylethanol (5.62 g, 46.0 mmol), EDCI (8.82 g, 46.0 mmol) and DMAP (0.561 g, 4.60 mmol) in CH2Cl2 (100 mL) was stirred at room temperature for 12 hours. The solvent was then concentrated and the residue partitioned with H2O-ethyl acetate. The phases were separated and the aqueous layer back-extracted with ethyl acetate (2×). The combined organic phases were washed (H2O, brine), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Biotage/0-20% ethyl acetate-hexane) to provide the title compound as a colorless oil (8.38 g, 92%). 1H NMR (400 MHz, CD3OD) δ 7.32-7.23 (m, 7H), 7.10-7.04 (m, 2), 5.85 (q, J=6.5 Hz, 1H), 3.71 (s, 2H), 1.48 (d, J=6.5 Hz, 3H).

출처