Ethyl vinyl ether → HCID 14882760, compound

Participants

Reaction Steps

To a solution of 4 g of 3β-(t-butyldimethylsilyloxy)androst-5-en-17β-ol in 50 ml of vinyl ethyl ether, there was added 0.25 g of mercuric acetate. The mixture was stirred at room temperature for 24 hours, quenched with triethylamine, and then poured into dilute aqueous potassium carbonate solution. The aqueous mixture was extracted 3 times with 100 ml-portions of diethyl ether and the combined organic extracts were washed with saturated aqueous sodium chloride solution and then dried over sodium sulfate. The solvent was then removed under reduced pressure and the residue was purified by flash chromatography using ethyl acetate/hexane, 1:4, to give 3β-(t-butyldimethylsilyloxy)-17β-ethenyloxyandrost-5-ene.

Provenance & Evidence