Hydrochloric Acid → 3-Methoxyestra-1,3,5(10),9(11)-tetraen-17-one

Participants

Reaction Steps

A solution of 0.5 gram of 3-methoxy-13β-methylgona-1,3,5 -(10)-trien-17-one, 0.5 milliliter of 2,6-dimethylpyridine, 1.97 grams of tetrabutylammonium fluoborate [(C4H9)4N-BF4 ] in 40 milliliters of acetonitrile, 10 milliliters of water and 10 milliliters of tetrahydrofuran was electrolyzed between a platinum anode having a surface area of 21 square centimeters and a nickel cathode having a surface area of 20 square centimeters while a potential of 1.7 volts measured at the anode against a saturated calomel standard electrode was maintained between the electrodes. At the completion of the electrolysis, which was established by thin-layer chromatography, the electrolyte solution was made slightly acid by adding hydrochloric acid thereto and the acidified solution was then allowed to stand at room temperature for a period between 20 and 30 minutes. Water was then added to the solution and the mixture was then extracted with diethyl ether. The ether layer was then separated, dried over anhydrous sodium sulfate, and the solid was distilled therefrom at a subatmospheric pressure. The residue was taken up in a mixture of dichloromethane and methanol and recrystallized therefrom. In this manner, 0.3 gram of 3-methoxy-13β-methylgona-1,3,5(10), 9(11)-tetraen-17-one having a melting point of 139°-143° C. was obtained.

Provenance & Evidence