Hydrochloric Acid → 21-Acetoxy-6-chloro-11beta-hydroxy-16alpha-methyl-1,4,6-pregnatriene-3,20-dione

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Reaction Steps

A hydrogen chloride stream is introduced into a solution of 1.0 g. of 21-acetoxy-6α-chloro-11β-hydroxy-16α-methyl-4-pregnene-3,20-dione in 100 ml. of dioxane for 30 minutes at 25° after adding 1.5 g. of dichlorodicyanobenzoquinone. The solution is then heated for 15 hours to 120°. After cooling, the solution is filtered, the filter cake washed with dichloromethane, and the filtrate evaporated under vacuum. The residue of the evaporation is chromatographed on silica gel. With 32-40% acetone-hexane, after recrystallization from acetone-diisopropyl ether, 380 mg. of 21-acetoxy-6-chloro-11β-hydroxy-16α-methyl-1,4,6-pregnatriene-3,20-dione is obtained.

Provenance & Evidence