تفاعل #81465

معادلة التفاعل

triethylamine

adrenosterone

tert-butyldimethylsilyl trifluoromethanesulfonate

→

title compound

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

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر