Benzoyl chloride → HCID 70447030, compound

Participants

Reaction Conditions

Reaction Steps

Aqueous N-sodium hydroxide solution (0.15 ml.) and benzoyl chloride (0.023 ml.) were successively added at 0° C. to a stirred solution of N-n-butyl-N-methyl-11-(3,17β-dihydroxyoestra-1,3,5(10)-trien-7α-yl)undecanamide (Example 2; 0.06 g.) in acetone (1 ml.) and the mixture was stirred at 0° C. for 30 minutes and poured into saturated aqueous sodium bicarbonate solution (10 ml.). The mixture was extracted three times with diethyl ether (15 ml. each time) and the combined extracts were washed with water (3 ml.), dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using a 3:2 v/v mixture of toluene and ethyl acetate as eluant. There was thus obtained as an oil N-n-butyl-N-methyl-11-(3-benzoyloxy-17β-hydroxyoestra-1,3,5(10)-trien-7α-yl)undecanamide, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Provenance & Evidence