Abstract
IN the course of an investigation of 6-chloro-3-benzoyloxy- Δ4-cholestene1, we have isolated a mono-benzoate (m.p. 153–154°) of cis-3: 4-dihydroxy-Î"5-cholestene (I) which differs considerably from the monobenzoate (m.p. 209–210°) of the cis-diol prepared by the method of Rosenheim and Starling2; the latter has been accorded the 3-monobenzoate structure on the seemingly substantial evidence that the cis-diol (I) gives an insoluble digitonide, whereas the monobenzoate, m.p. 209–210°, fails to do so. To test the implication that the new ester, m.p. 153–154°, is the 4-monobenzoate, its reaction with digitonin was examined. It fails to give a digitonide using standardized conditions which effect immediate precipitation of the digitonides of cholesterol and the cis-diol (I). It follows that the formation of one of the monobenzoates of the cis-diol has been accompanied by the migration of a benzoyl-group from the C3- to the C4-hydroxyl, and although such migration appears to be less likely in the case of the monobenzoate m.p. 209–210°, the exact location of the esterified hydroxyl group in the mono-esters3 remains to be rigidly established. Furthermore, it is clear that the introduction of a C4-cis-benzoyloxy-group into cholesterol prohibits the digitonin reaction.
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Spring, F. S., and Swain, G., J. Chem. Soc., 1356 (1939).
J. Chem. Soc., 377 (1937).
(Added in proof). Dr. O. Rosenheim informs us (private communication) that he has prepared the hitherto unknown 4(?)-monoacetate of the cis-diol which, as we find is the case with the 3(?)-monoacetate, fails to give an insoluble digitonide.
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SPRING, F., SWAIN, G. Formation of Insoluble Digitonides of Cholesterol Derivatives. Nature 146, 718 (1940). https://doi.org/10.1038/146718b0
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DOI: https://doi.org/10.1038/146718b0
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