Reacción #1772024

Ecuación de reacción

2-fluorophenylacetic acid

(S)-1-phenylethanol

EDCI

→

title compound

Rendimiento 92.0%

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

Rendimiento 92.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe solvent was then concentrated
2. 2
   Otrothe residue partitioned with H2O-ethyl acetate
3. 3
   OtroThe phases were separated
4. 4
   Extracciónthe aqueous layer back-extracted with ethyl acetate (2×)
5. 5
   LavadoThe combined organic phases were washed (H2O, brine)
6. 6
   Secadodried (Na2SO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   OtroThe residue was purified by silica gel chromatography (Biotage/0-20% ethyl acetate-hexane)

Procedimiento

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).

Fuente