反応 #81465

反応方程式

triethylamine

adrenosterone

tert-butyldimethylsilyl trifluoromethanesulfonate

→

title compound

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

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他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
   その他after which time an oil separated
5. 5
   その他The ether phase was decanted off the oil
6. 6
   その他the solvent evaporated

実験手順

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).

出典