Reaction #1772024

Reaction equation

2-fluorophenylacetic acid

(S)-1-phenylethanol

EDCI

→

title compound

Yield 92.0%

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

Yield 92.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   ConcentrationThe solvent was then concentrated
2. 2
   Otherthe residue partitioned with H2O-ethyl acetate
3. 3
   OtherThe phases were separated
4. 4
   Extractionthe aqueous layer back-extracted with ethyl acetate (2×)
5. 5
   WashThe combined organic phases were washed (H2O, brine)
6. 6
   Dryingdried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   OtherThe residue was purified by silica gel chromatography (Biotage/0-20% ethyl acetate-hexane)

Procedure

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).

Source