反应详情

To a solution of 25.6 g of 19-acetoxyandrost-4-ene-3,17-dione in 4 liters of methanol cooled to 0° C. is added 3.1 g of sodium borohydride, and the mixture is stirred at 0° C. for one hour after which 30 ml of acetic acid is added and the methanol removed under reduced pressure. The resulting residue is taken up in ethyl acetate and washed with water. The organic layer is dried over magnesium sulfate, filtered and the solvent removed. The solid residue is dissolved in 2 liters of chlorofrom treated with 125 g of manganese dioxide and stirred for two hours. The reaction mixture is filtered, and the solvent removed under reduced pressure. The residue is chromatographed on alumina using benzene-ether (1:1) as the eluant. The product is recrystallized from acetone-hexane to give 19-acetoxy-17β-hydroxyandrost-4-en-3-one, M.P. 125°-127° C.

1. additionis added
2. customthe methanol removed under reduced pressure
3. washwashed with water
4. dry with materialThe organic layer is dried over magnesium sulfate
5. filtrationfiltered
6. customthe solvent removed
7. dissolutionThe solid residue is dissolved in 2 liters of chlorofrom
8. additiontreated with 125 g of manganese dioxide
9. filtrationThe reaction mixture is filtered
10. customthe solvent removed under reduced pressure
11. customThe residue is chromatographed on alumina
12. customThe product is recrystallized from acetone-hexane