ON STEROIDS - PART CD - LENGTHENING OF THE ALKYL CHAIN IN STEROID O-(OMEGA-CARBOXYALKYL)OXIMES BY WITTIG REACTION

The steroid O-alkyloximes with various alkyl length (2-4 carbons) and with terminal hydroxyl groups were oxidized to aldehydes and their Wit tig reaction with triethyl phosphonoacetate was studied. Grimes derive d from 17-oxoandrost-5-en-3 beta-yl acetate and from 7-oxo and 19-oxoc holest-5-en-3 beta-yl acetate were used. Except of 7- and 19-[O-(2-hyd roxyethyl)]oximes, all the hydroxyalkyloximes gave successively aldehy des and corresponding unsaturated esters. The method is useful for the lengthening of the carbon chain in omega-substituted O-alkyloximes.