Réaction #46640

Équation de réaction

2-fluorophenylacetic acid

(S)-1-phenylethanol

EDCI

→

title compound

Rendement 92.0%

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

Rendement 92.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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