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The Bamford-Stevens reaction of 3 -acetoxy-5a-cholestan-6-one tosylhydrazone


, : The Bamford-Stevens reaction of 3 -acetoxy-5a-cholestan-6-one tosylhydrazone. Aust J Chem 21(2): 527-530

The title compound (I) was subjected to the conditions of the Bamford-Stevens reaction. The crude product thus obtained on acety-lation, followed by chromatography over neutral alumina, gave choles-teryl acetate (II), 3[beta]-acetoxy-5a-cholestan-6a-yl 2-acetoxyethyl ether (III), and 3[beta]-acetoxy-5a-cholestan-6a-yl 2-hydroxyethyl ether (IV), an artefact of (III). The structures assigned to the compounds (III) and (IV) are compatible with the spectral data (IR and n. m. r. [nuclear magnetic resonance]), interconversions, and degradative studies. When passed over neutral alumina, (III) was partly changed into (IV) and the latter on acetylation regenerated (III).

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