反応 #1772024

反応方程式

2-fluorophenylacetic acid

(S)-1-phenylethanol

EDCI

→

title compound

収率 92.0%

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

収率 92.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   濃縮The solvent was then concentrated
2. 2
   その他the residue partitioned with H2O-ethyl acetate
3. 3
   その他The phases were separated
4. 4
   抽出the aqueous layer back-extracted with ethyl acetate (2×)
5. 5
   洗浄The combined organic phases were washed (H2O, brine)
6. 6
   乾燥dried (Na2SO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The residue was purified by silica gel chromatography (Biotage/0-20% ethyl acetate-hexane)

実験手順

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).

出典