反应详情

A solution of 17β,19-dihydroxy-1α-methyl-4,6-androstadien-3-one diacetate in anhydrous tetrahydrofuran is added slowly to an ice cold ethereal solution of lithium dimethylcopper prepared as in the preceding Example. Stirring is continued for 30 minutes and the mixture is poured onto a saturated aqueous ammonium chloride solution. Benzene is added and the mixture filtered through a bed of diatomaceous earth. The organic layer is washed with aqueous ammonium chloride, water, dried over magnesium sulfate and evaporated to dryness. The residue is stirred at room temperature with aqueous methanolic hydrochloric acid for 1 hour and then poured onto ice water. The gum is extracted with ether, washed with water, dried over magnesium sulfate and the ether removed. The residue is chromatographed on silica gel and eluted with benzene. The eluant is recrystallized from hexane to give 17β,19-dihydroxy-1α,7α-dimethyl-4-androsten-3-one diacetate.

1. filtrationthe mixture filtered through a bed of diatomaceous earth
2. washThe organic layer is washed with aqueous ammonium chloride, water
3. dry with materialdried over magnesium sulfate
4. customevaporated to dryness
5. stirringThe residue is stirred at room temperature with aqueous methanolic hydrochloric acid for 1 hour
6. additionpoured onto ice water
7. extractionThe gum is extracted with ether
8. washwashed with water
9. dry with materialdried over magnesium sulfate
10. customthe ether removed
11. customThe residue is chromatographed on silica gel
12. washeluted with benzene
13. customThe eluant is recrystallized from hexane