Hydrochloric Acid → HCID 13061708, compound

Participants

Reaction Steps

To a solution of 0.60 g (0.00188 mol) of (Z)-3α,5β,7α-pregn-17(20)-ene-3,7-diol and 30 ml of dry toluene was added 1.8 ml (ca. 1.84 g=0.023 mol) of dry pyridine, 1.8 ml (ca. 1.66 g=0.016 mol) of acetic anhydride and 0.016 g (0.00013 mol) of 4-dimethylaminopyridine. The mixture was stirred under argon atmosphere for 18 hr. and then poured into 100 ml of water, acidified with 1 N HCl and extracted with 3×50 ml of ethyl acetate. The combined organic phases were washed with water until neutral and then dried over anhydrous sodium sulfate. Filtration and evaporation of the solvent in vacuo gave 0.789 g of crude product. TLC revealed an incomplete reaction so the above procedure was repeated. The product was recrystallized from methanol to afford 0.566 g (75%) of (Z)-3α,5β,7α-pregn-17(20)-ene-3,7-diol diacetate. The analytical sample, recrystallized twice from methanol, had mp 92°-93° C.

Provenance & Evidence