反応 #7391

反応方程式

4-chloro-3-hydroxy-benzaldehyde

tert-butyldimethylsilyl chloride

triethylamine

→

title compound

3-{[tert-Butyl(dimethyl)silyl]oxy}-4-chlorobenzaldehyde

溶媒

DCM

反応条件

後処理

1. 1
   その他The mixture was quenched with saturated aqueous sodium bicarbonate
2. 2
   抽出extracted with diethyl ether
3. 3
   濃縮The combined organic extracts were concentrated under reduced pressure
4. 4
   その他to give an oil which
5. 5
   その他was purified
6. 6
   洗浄SPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate-cyclohexane)

実験手順

A mixture of 4-chloro-3-hydroxy-benzaldehyde* (0.354 g), 4-N,N-dimethylaminopyridine (0.028 g), tert-butyldimethylsilyl chloride (0.409 g) and triethylamine (0.473 ml) in DCM (15 ml) was stirred at room temperature under nitrogen for 19 h. The mixture was quenched with saturated aqueous sodium bicarbonate and extracted with diethyl ether. The combined organic extracts were concentrated under reduced pressure to give an oil which was purified using SPE (silica, eluting with cyclohexane followed by 10% to 30% ethyl acetate-cyclohexane) to give the title compound (0.42 g) as an oil. *Kelley, J; Linn, J; Selway, J. W. T., J. Med. Chem. (1989), 32(8), 1757–63.

出典