Ethyl Acetate → HCID 70565263, compound

Participants

Reaction Steps

A solution of 6-ethylenedioxy-5α-cholestan-3β-(3, 12.5 g) in pyridine was added to ice-cold pyridine-CrO3 complex prepared by adding CrO3 (182 g) to ice-cold pyridine (182 ml). An additional amount of pyridine (90 ml) was utilized for complete transfer. The mixture was allowed to come to room temperature and stirred for 10 hr. It was then brought to a volume of 500 ml with ethyl acetate and filtered through a column packed with Celite (a diatomaceous silica product marketed by Johns-Manville Co.) (50 g, 4 cm diameter) slurried in ethyl acetate. Material eluted with a total of 750 ml of ethyl acetate was collected, and filtered through a 6 cm column packed with alumina (100 g) slurried in ethyl acetate. After elution with 1200 ml of ethyl acetate and evaporation of the solvent, a greenish solid was recovered. This was applied to a 2×23.5 cm (50 g alumina, AG-7 minus 200 mesh) column and eluted with ethyl acetate. The first 150 ml of eluant gave 12.3 g (98%) of pure 6,6-ethylenedioxy-5α-cholestan-3-one (4). An analytical sample recrystallized from MeOH was obtained as white crystals: m.p. 115°-116°; nmr (CDCl3) δ 2.35 (m, C-2 and C-4 protons), 3.9 (m, ketal); ir (KBr) 1710 cm+1 (C=O); mass spectrum: m/e 444 (M+, 19%, C29H48O3 : C, 78.33; H, 10.88; obs: C, 78.37; H, 10.93.

Provenance & Evidence