反応 #67302

反応方程式

1-(5-bromo-3-chloro-2-hydroxyphenyl)ethanone

(2R)-(−)Glycidyltosylate

K2CO3

water

→

title compound

収率 74.7%

1-[5-BROMO-3-CHLORO-2-(OXIRAN-2-YLMETHOXY)PHENYL]ETHANONE

収率 74.7%

溶媒

DMF

EtOAc

反応条件

後処理

1. 1
   その他was brought to ambient temperature
2. 2
   抽出The water phase was extracted with EtOAc
3. 3
   洗浄The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine
4. 4
   乾燥dried (Na2SO4)
5. 5
   その他evaporated to dryness
6. 6
   その他Purification on flash column chromatography (isooctane/EtOAc)

実験手順

A mixture of 1-(5-bromo-3-chloro-2-hydroxyphenyl)ethanone (5.5 g, 21.9 mmol), (2R)-(−)Glycidyltosylate (10 g, 43.8 mmol) and K2CO3 (4.5 g, 32.9 mmol) in DMF (25 ml) was heated at 60° C. for 25 h. The solution was brought to ambient temperature and water and EtOAc was added. The water phase was extracted with EtOAc. The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine and then dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (5.0 g). MS m/z (rel. intensity, 70 eV) 250 (30), 248 (M+, 26), 235 (bp), 233 (85), 57 (90), 306 (M+, 9).

出典