反应详情

A mixture of dihydrotestosterone (1.00 g), 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) or SELECTFLUOR® (1.92 g) in i-PrOH (35 ml) was refluxed for 18 h. After cooling, the resulting precipitate was filtered and the organic phase was washed with H2O and brine, dried over Na2SO4 and was evaporated to dryness. The crude reaction mixture was purified by flash chromatography (SiO2, n-hexane/acetone/EOAc 75/12.5/12.5) to give 4α-fluoro-17β-hydroxyandrostan-3-one (43 mg, 4% yield).

1. temperaturewas refluxed for 18 h
2. temperatureAfter cooling
3. filtrationthe resulting precipitate was filtered
4. washthe organic phase was washed with H2O and brine
5. dry with materialdried over Na2SO4
6. customwas evaporated to dryness
7. customThe crude reaction mixture
8. customwas purified by flash chromatography (SiO2, n-hexane/acetone/EOAc 75/12.5/12.5)