5α-Cholestan-3-one reacted with chlorotrimethylsilane and zinc dust in ether or tetrahydrofuran to give 5α-cholest-2-ene. 17β-Acetoxy-5α-androstan-3-one and methyl 3-oxo-5β-cholanate behaved similarly, but examples of 6-, 7-, 12-, 17-, and 20-oxo-steroids did not react. Diones containing a 3-oxo-group reacted selectively at the 3-position.
P. Hodge and M. N. Khan, J. Chem. Soc., Perkin Trans. 1, 1975, 809 DOI: 10.1039/P19750000809
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