反应详情

Methyl androst-4-ene-3-one-17β-carboxylate (10 g, 30.3 mmol, prepared according to Rasmusson, et al., J. Med. Chem. 27 1960 (1984)) and chloranil (8.95 g, 36.4 mmol) in 700 ml t-butanol was heated at reflux for 3.5 hours then cooled and filtered. The filtrate was concentrated and the residue taken up in 700 ml chloroform and washed successively with 4×150 ml water, 3×150 ml saturated sodium bicarbonate, 3×150 ml 5% sodium hydroxide, 3×150 ml brine, dried over sodium sulfate, and concentrated to yield methyl androst-4,6-diene-3-one-17β-carboxylate as a dark foam (7.0 g, 70%).

1. temperatureat reflux for 3.5 hours
2. temperaturethen cooled
3. filtrationfiltered
4. concentrationThe filtrate was concentrated
5. washwashed successively with 4×150 ml water, 3×150 ml saturated sodium bicarbonate, 3×150 ml 5% sodium hydroxide, 3×150 ml brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated