Diethyl Ether → 1,16beta-Diacetoxy-3-methoxyestra-1,3,5(10)-trien-17-one

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Reaction Steps

Lead tetraacetate (0.65 g) is added to a solution of 1,17-diacetoxy-3-methoxyestra-1,3,5(10),16-tetraene (0.5 g, 1.3 mM) in 0.5 ml acetic anhydride and 10 ml glacial acetic acid with stirring. Solution occurs after 1 hr and stirring is continued at room temperature for 16 hrs. The resulting dark brown solution is evaporated in vacuo at 40° to give an oily residue which is dissolved in 150 ml of benzene. The benzene solution is then washed with H2O, 5% NaHCO3 and saturated NaCl solution. The organic layer is dried over MgSO4 and evaporated in vacuo to give a white solid. Trituration with ether gives 1,16β-diacetoxy-3-methoxyestra-1,3,5(10)-trien-17-one as a white solid, yield 0.31 g (62%). Recrystallization from methanol gives 1,16β-diacetoxy-3-methoxyestra-1,3,5(10)-trien-17-one having a m.p. of 191°-192°.

Provenance & Evidence