Abnormal products obtained during an attempted substitution of 3.alpha.,5-cyclo-6.beta.-methoxy-5.alpha.-23,24-bisnorcholan-22-ol tosylate with a Grignard reagent involving .gamma.,.gamma.-dimethylallyl bromide

Attempted coupling of 6..beta..-methoxy-3..cap alpha..,5-cyclo-5..cap alpha..-23,24-bisnorcholan-22-yl tosylate with gamma,gamma/sup -/ dimethylallyl bromide in the presence of magnesium leads to the formation of 22,22'-bis-6..beta..-methoxy-3..cap alpha..,5-cyclo-5..cap alpha..-bisnorcholanyl, a novel disteroid, and 3..cap alpha..,5-cyclo-5..cap alpha..-23,24-bisnorcholan-6..beta..-yl methyl ether rather than to the expected desmosterol derivatives. The formation of these products has been attributed to a common 22-bisorcholanylmagnesium bromide intermediate which undergoes Wurtz-type coupling or is hydrolyzed to an alkane during work-up.