反应 #81465

反应方程式

triethylamine

adrenosterone

tert-butyldimethylsilyl trifluoromethanesulfonate

→

title compound

3-(tert-Butyldimethylsiloxy)androsta-3,5-diene-11,17-dione

溶剂

dichloromethane

反应条件

后处理

1. 1
   其他The dichloromethane was evaporated
2. 2
   workup.DISSOLUTIONthe residue redissolved in diethyl ether (100 ml)
3. 3
   workup.WAITto stand for 30 min
4. 4
   其他after which time an oil separated
5. 5
   其他The ether phase was decanted off the oil
6. 6
   其他the solvent evaporated

实验过程

To a solution of adrenosterone (6.0 g, 20 mmol) in dry, dichloromethane (120 ml) was added triethylamine (8.4 ml, 60 mmol) followed by tert-butyldimethylsilyl trifluoromethanesulfonate (5.0 ml, 22 mmol) and the mixture stirred at room temperature for 3 h. The dichloromethane was evaporated and the residue redissolved in diethyl ether (100 ml), then allowed to stand for 30 min, after which time an oil separated. The ether phase was decanted off the oil and the solvent evaporated to give the title compound which was used directly in step (b). IR νmax 1705, 1747 cm-1 ; 1H-NMR(CDCl3) inter alia δ0.12 (6H,s,Me2Si), 0.85 (3H,s,18-CH3), 0.92 (9H,s,tBuSi) 1.17(3H,s, 19-CH3), 4.73 (1H,dm, J 6.9Hz, 6-H), 5.36 (1H,m,4-H).

来源