No abstract

No abstract

No abstract

No abstract

No abstract

No abstract

No abstract

was refluxed vigorously under argon for 20 hours. The catalyst was removed with suction and washed with hot chloroform. The very dark filtrate was concentrated, chromatographed on alumina and the strongly fluorescent zone (ultraviolet light) eluted with chloroform. Concentrating with addition of ethanol gave 169 mg. (17%) of yellow prisms, m.p. 269-270'.Vacuum sublimation, followed by repeated chromatography and two recrystallizations from chloroform ethanol provided tiny faintly yellowish needles, m.p. 271-272'.Anal. Calcd. for C13Hf008: C, 65.09; H , 4.75; OCH3, 29.25. Found: C, 64.85; H, 4.86; OCH3, 29.46. Attempts to prepare this compound by dehydrogenation with lead tetraacetatel1J9 were unsuccessful. Only a trace of material with blue fluorescence, indicative of a naphthalene derivative, was formed. RECEIVED JULY 17, 1953llaand 118-hydroxytestosterone have been prepared from 1 la-hydroxy-4-androstene-3,17-dione and adrenosterone, respectively, by the formation of the Cr-enamine, reduction of the free carbonyl groups with lithium aluminum hydride and subsequent hydrolysis to regenerate the 3-keto-A'-system. 1 la-Hydroxytestosterone thus prepared was readily acylated at the Cl7hydroxyl position and the resulting llp-hydroxy-17-ester upon oxidation yielded the 11-keto-17-ester which was saponified to 11-ketotestosterone. Under certain conditions adrenosterone gave a Ca.17-bispyrrolidyl enamine which upon reduction and subsequent hydrolysis yielded 11~-hydroxyandrostene-3,17-dione.