2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 54187257, compound

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Reaction Steps

The 25-hydroxycholesterol was dissolved in dioxane and boiled with 2,3-dichloro-5,6-dicyanobenzo-quinone (DDQ) to obtain 25-hydroxycholesta-1,4-diene-3-one. This latter compound was subjected to dehydrogenation with chloroanil in the presence of the reduced derivative of DDQ-hydroquinone (2HDDQ) to obtain 25-hydroxy-cholesta-1,4,6-triene-3-one. Alternatively, 25-hydroxy-cholesta-1,4,6-trien-3-one can be obtained by DDQ oxidation of 25-hydroxycholesterol (J. J. Partridge et al., Helv. Chim. Acta 57, 764 (1974) which was converted from 6β-methoxy-25-hydroxy-3α,5-cyclo-5α-cholestane.

Provenance & Evidence