تفاعل #1772024

معادلة التفاعل

2-fluorophenylacetic acid

(S)-1-phenylethanol

EDCI

→

title compound

المردود 92.0%

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

المردود 92.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   تركيزThe solvent was then concentrated
2. 2
   أخرىthe residue partitioned with H2O-ethyl acetate
3. 3
   أخرىThe phases were separated
4. 4
   استخلاصthe aqueous layer back-extracted with ethyl acetate (2×)
5. 5
   غسيلThe combined organic phases were washed (H2O, brine)
6. 6
   تجفيفdried (Na2SO4)
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe residue was purified by silica gel chromatography (Biotage/0-20% ethyl acetate-hexane)

الإجراء التجريبي

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).

المصدر