2,6-Lutidine → 3-Methoxy-13beta-methyl-17,17-(ethylenedioxy)gona-1,3,5(10),9(11)-tetraene

Participants

Reaction Steps

A solution of 2.3 grams of 3-methoxy-13β-methyl-17,17-(ethylenedioxy)gona-1,3,5(10)-triene, 1.1 milliliters of 2,6-dimethylpyridine, and 1.4 grams of tetraethylammonium perchlorate in 45 milliliters of N,N-dimethylformamide and 50 milliliters of methanol was electrolyzed between the same pair of electrodes that were described in Example 1, spaced from each other at a distance of 1.5 centimeters, with a current of 600 milliamperes for a period of 55 minutes. At the end of the electrolysis all traces of methanol were distilled from the solution at a subatmospheric pressure and the solution was then acidified with anhydrous p-toluenesulfonic acid, allowed to stand at room temperature for a period between 20 and 30 minutes and then made alkaline with a saturated solution of sodium bicarbonate. A portion of the product precipitated during the addition of the bicarbonate solution and water was then added to complete its precipitation. In this manner, 1.8 grams of 3-methoxy-13β-methyl-17,17-(ethylenedioxy)gona-1,3,5-(10),9(11)-tetraene having a melting point of 146°-149° C. was obtained.

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