Ammonium Chloride → HCID 56609027, compound

Participants

Reaction Conditions

Reaction Steps

At 0° C. under argon, 40 ml of a 5% solution of methyllithium in ether is added dropwise to a suspension of 9.3 g of copper(I) iodide in 186 ml of anhydrous tetrahydrofuran. The yellow solution is cooled to -30° C., and a solution of 7.4 g of 11β,17-dihydroxy-6α-methyl-21-valeryloxy-4-pregnene-3,20-dione in 186 ml of anhydrous tetrahydrofuran is added thereto. The mixture is agitated for 10 minutes at -25° C. and poured on an aqueous ammonium chloride solution. After extraction with methylene chloride, the organic solution is washed, dried over sodium sulfate, and evaporated under vacuum. The crude product is purified on 600 g of silica gel with a methylene chloride-acetone gradient (0-20% acetone), thus isolating 4.6 g of 11β,21-dihydroxy-6α-methyl-17-valeryloxy-4-pregnene-3,20-dione, mp 160° C.

Provenance & Evidence