Methanol → 6-Chloro-11beta,21-dihydroxy-16alpha-methyl-4,6-pregnadiene-3,20-dione

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Reaction Steps

A solution of 2.95 g. of 21-acetoxy-6-chloro-11β-hydroxy-16α-methyl-4,6-pregnadiene-3,20-dione in 80 ml. of methanol is combined with 800 mg. of potassium carbonate and stirred for 5 minutes at room temperature under argon. After adding 5 ml. of acetic acid and 5 ml. of water, the reaction solution is completely evaporated under vacuum. The residue is chromatographed on silica gel. With 42-50% acetone-hexane and after recrystallization from acetone-diisopropyl ether, 1.55 g. of 6-chloro-11β,21-dihydroxy-16α-methyl-4,6-pregnadiene-3,20-dione is obtained, m.p. 229° [α]D25 =+175° (methanol). UV: ε285 =19,850 (methanol).

Provenance & Evidence