Реакция #1772024

Уравнение реакции

2-fluorophenylacetic acid

(S)-1-phenylethanol

EDCI

→

title compound

Выход 92.0%

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

Выход 92.0%

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   КонцентрированиеThe solvent was then concentrated
2. 2
   Другоеthe residue partitioned with H2O-ethyl acetate
3. 3
   ДругоеThe phases were separated
4. 4
   Экстракцияthe aqueous layer back-extracted with ethyl acetate (2×)
5. 5
   ПромывкаThe combined organic phases were washed (H2O, brine)
6. 6
   Сушкаdried (Na2SO4)
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated in vacuo
9. 9
   ДругоеThe residue was purified by silica gel chromatography (Biotage/0-20% ethyl acetate-hexane)

Методика

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).

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