Potassium Carbonate → 1-Acetoxy-16alpha-chloro-3-methoxyestra-1,3,5(10)-trien-17-one

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Reaction Steps

A solution of Cl2 (0.162 g, 2.3 mM) in 5 ml of carbon tetrachloride is added over a period of 30 min to a stirred suspension of 1,17-diacetoxy-3-methoxyestra-1,3,5(10),16-tetraene (0.77 g, 2 mM), K2CO3 (5 g) and 25 ml of CCl4 at 0°. Dilute aqueous sodium thiosulfate is then added, the layers are separated and the aqueous layer is extracted with 2 × 50 ml chloroform. The organic layers are combined, dried over MgSO4 and evaporated in vacuo. The residue is triturated with ether to give a white solid. Recrystallization from methanol gives 1-acetoxy-16α-chloro-3-methoxyestra-1,3,5(10)-trien-17-one, yield 0.64 g (76%); m.p. 194.5°-196°.

Provenance & Evidence