反应详情

To a solution of 3,17β-dihydroxyestra-1,3,5(10)-triene-4-carboxaldehyde (2b, 0.300 g, 1.0 mmol) in acetone (10 mL) was added Jones reagent (0.50 mL) at 0° C. The reaction mixture was stirred for 10 min, quenched with 2-propanol, and extracted with EtOAc. The combined organic layers were washed with H2O, then with saturated aqueous NaCl, and dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:THF (4:1→2:1, v/v) to afford 0.276 g of 12 (93% yield), m.p. 234°-237° C.

1. customquenched with 2-propanol
2. extractionextracted with EtOAc
3. washThe combined organic layers were washed with H2O
4. dry with materialwith saturated aqueous NaCl, and dried (Na2SO4)
5. filtrationThe desiccant was filtered
6. customthe solvent was evaporated at reduced pressure
7. customThe residue was purified by column chromatography (silica gel)