Reactions of cyclohexanone with NaH and Me3SiCl in various solvents yielded predominantly (90-97%) the silyl enol ether 2 resulting from enolization, with only a few percent of the alkyl silyl ether 1 resulting from initial reduction. Similar reactions with KH and Me3SiCl proceeded well only in dioxane to give >99% of 2. Cyclohexanone, 2-methylcyclohexanone, acetophenone, 2-heptanone were converted to trimethylsilyl enol ethers in good yields by this method.
ASJC Scopus subject areas
- Organic Chemistry