反应详情

A solution of androstane-3β,5α,17β-triol (0.48 g) and IBX (0.72 g) in DMSO (8 mL) was stirred at −15° C. overnight and then quenched at room temperature by addition of H2O (40 mL). After stirring for 15 min, the mixture was filtered and the cake was washed with EtOAc. The layers were separated, and the aqueous phase was extracted with EtOAc (3×40 mL). The combined organic extracts were dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20) to give the title compound II-ad (0.36 g, 75%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 3.48 (s, 1H), 2.72 (d, 1H), 2.60-1.18 (m, 20H), 1.23 (s, 3H), 0.86 (s, 3H).

1. customquenched at room temperature by addition of H2O (40 mL)
2. filtrationthe mixture was filtered
3. washthe cake was washed with EtOAc
4. customThe layers were separated
5. extractionthe aqueous phase was extracted with EtOAc (3×40 mL)
6. dry with materialThe combined organic extracts were dried over Na2SO4
7. customevaporated to dryness
8. customThe residue was purified by flash chromatography (SiO2, n-hexane/CH2Cl2/acetone 60/20/20)