Reaction #6822

Reaction equation

2-(3-chloro-4-hydroxy-phenyl)-acetamide

imidazole

tert-butyldimethylsilyl chloride

→

2-[4-(tert-butyldimethylsilanyloxy)-3-chlorophenyl]acetamide

Yield 77.4%

Solvents

dimethylformamide

ethyl acetate

Conditions

Workup

1. 1
   Washwashed with 50 mL of sodium carbonate
2. 2
   OtherThe ethyl acetate was evaporated

Procedure

A solution of 2-(3-chloro-4-hydroxy-phenyl)-acetamide (100 mg), imidazole (184 mg), and tert-butyldimethylsilyl chloride (163 mg) was stirred for 2 h in 5 mL of dimethylformamide. The solution was diluted with 50 mL of ethyl acetate and washed with 50 mL of sodium carbonate. The ethyl acetate was evaporated to afford 125 mg of 2-[4-(tert-butyldimethylsilanyloxy)-3-chlorophenyl]acetamide.

Source