Sodium Iodide → 17beta-Acetoxymethoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

Participants

Reaction Steps

3α-Hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (1g.) was warmed with tetra-butyl ammonium hydroxide (1.94g. Of 40% solution) and acetone (10 ml.) to effect solution. The solution was refluxed with sodium iodide (100 mg.). potassium bicarbonate (150 mg.) and chloromethyl acetate (0.6 ml.) for 2 hours. The mixture was evaporated to small volume, diluted with ethyl acetate, washed with water, dried (Na2SO4) and evaporated to a residue. Purification by preparative t.l.c. gave title compound (less polar band) (318 mg.) as white foam; [α]D + 52°.

Provenance & Evidence