2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 21-Acetoxy-6alpha-chloro-11beta-hydroxy-16alpha-methyl-1,4-pregnadiene-3,20-dione

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Reaction Steps

2.0 g of 21-acetoxy-6α-chloro-11β-hydroxy-16α-methyl-4-pregnene-3,20-dione is dissolved in 100 ml of dioxane; 3 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is added thereto and the mixture heated for 24 hours to boiling. After cooling, the mixture is vacuum-filtered from the undissolved matter, washed with dichloromethane, and concentrated under vacuum. The crude product is chromatographed on silica gel. With 37-46% acetone-hexane, after recrystallization from acetone-diisopropyl ether, 1.08 g of 21-acetoxy-6α-chloro-11βhydroxy-16α-methyl-1,4-pregnadiene-3,20-dione is obtained, m.p. 208.5° C. [α]D25 =+90° (chloroform). UV: ε243 =15,700 (methanol).

Provenance & Evidence