Symmetrical Ketones from Aldehyde Trimethylsilyl Enol Ethers on Storage: A Cautionary Note

Abstract

The widespread use of trialkylsilyl enol ethers has dramatically increased the utility of enolate anion chemistry.¹ These enol ethers are readily prepared, reactive, and in many instances are stable enough to be commercially available. We have been using trimethylsilyl enol ethers as aldehyde enolate precursors and wish to report some observations regarding storage of these 1-alkyl-2-trimethylsilyloxyethenes. We have noted that after 2–3 months in sealed glass ampuoles these trimethylsilyl enol ethers contained significant amounts of symmetrical ketones.