HCID 57236229, compound → HCID 53668100, compound

Participants

Reaction Steps

Jones reagent (2.67M, 2.0 mL. 5.3 mmol) was added to a solution of 20,21 -dimethylpregna-5,20-dien-3β-ol (6, 460.1 mg, 1.400 mmol) in 50 mL of acetone and the reaction was stirred 45 min. After quenching with 2-propanol (1.0 mL) the mixture was poured into 100 mL of water and extracted three times with 50 mL of ethyl acetate. The combined organic extracts were washed with 50 mL of saturated sodium bicarbonate+50 mL of brine, dried over magnesium sulfate, and filtered through Celite. The residue was washed with 25 mL of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Flash chromatography (25% ethyl acetate/hexanes on silica gel) and recrystallization of the residue from 95% ethanol gave yellow needles (138.2 mg, 0.4059 mmol, 29%), m.p. 172°-178° C. (NA-1993B-73)

Provenance & Evidence