Iodine trifluoroacetate, generated from iodine and silver trifluoroacetate, adds stereospecifically to 5α-cholest-2-ene to give 3α-iodo-5α-cholestan-2β-yl trifluoroacetate (II) in 72% yield. Further reactions of this product provide convenient preparations of 5α-cholestan-2β-ol (III), 2β,3β-epoxy-5α-cholestane (IV), and 5α-cholestane-2β,3β-diol (VI; R = H).
D. G. Hey, G. D. Meakins and M. W. Pemberton, J. Chem. Soc. C, 1966, 1331 DOI: 10.1039/J39660001331
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