The reduction of 3-acetoxy-4-methoxycholesta-3,5-diene with sodium borohydride in aqueous ethanol gave 3β-hydroxy-4-methoxycholest-4-ene as sole isolable product. This reaction is discussed in terms of current theories on the protonation of dienolate ions.
G. H. Whitham and J. A. F. Wickramasinghe, J. Chem. Soc. C, 1968, 338 DOI: 10.1039/J39680000338
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