Oxalyl chloride → 17beta-Chlorocarbonyl-5alpha-androstan-3-one

Participants

Reaction Steps

A solution of 5α-androstan-3-one 17β-carboxylic acid (2.1 g., corrected for the presence of 15% 5α-pregnan-3,20 -dione) and oxalyl chloride (4 ml.) in dry benzene (125 ml.) was refluxed for 1.5 hours before evaporation to dryness to afford crude 17β-chlorocarbonyl-5α-androstan-3-one. Morpholinoethanol (5 ml.) was added to a stirred solution of the acid chloride in dry ether (125 ml.) and pyridine (3 ml.) at room temperature. After 1 hour the mixture was diluted with ether (100 ml.) and washed with aqueous 10% sodium hydroxide and water, dried (MgSO4), filtered and evaporated to give a gum (3.275 g.). A sample (2.0 g.) gave, after purification by preparative t.l.c. (ethanol/chloroform 1:19) title compound (900 mg.) as a white froth; [α]D + 54.5°, (c. 0.9).

Provenance & Evidence