反应详情

A solution of androst-4-ene-3,17-dione in t-butanol was heated to boiling and added to a boiling solution of potassium t-butoxide in t-butanol. Methyl chloride in t-butanol was added slowly. The solution was cooled, acidified with concentrated hydrochloric acid, and diluted with water. The excess t-butanol was removed under vacuum and the aqueous layer extracted with ethylacetate. The combined extracts were washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel and eluted with hexane/ethylacetate. The eluant was evaporated and the residue crystallized from ether to yield 4-methylandrost-4-ene-3,17-dione; I.R. (KBr): 1735 (17-oxo), 1660 (3-oxo), 1620 cm-1 (Δ4).

1. temperatureThe solution was cooled
2. customThe excess t-butanol was removed under vacuum
3. extractionthe aqueous layer extracted with ethylacetate
4. washThe combined extracts were washed with water
5. dry with materialdried over magnesium sulfate
6. customevaporated in vacuo
7. customThe residue was chromatographed on silica gel
8. washeluted with hexane/ethylacetate
9. customThe eluant was evaporated
10. customthe residue crystallized from ether