Ring–Chain Tautomerism of 5-Oxo-3,5-seco-A-norcholestan-3-ol

Abstract
5-Oxo-3,5-seco-A-norcholestan-3-ol (4) was prepared in four steps from Windaus' keto-acid (1; R = H), and found to exist almost completely in the tautomeric hemiketal form 5. With ethanol and a trace of acid this affords the ethyl ketals 6a, 6b; under equilibrium conditions the ratio of 6a:6b is about 4:1.

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