New Methods and Reagents in Organic Synthesis. 18. Homologation of Ketones with Trimethylsilyldiazomethane (TMSCHN2)

Abstract

Trimethylsilyldiazomethane (TMSCHN2) easily reacts with various ketones in the presence of boron trifluoride etherate in methylene chloride solution to give chain- or ring-homologated ketones, and can be used as a stable and safe substitute for hazardous diazomethane. The reaction proceeds below 0°C during 1–4 h, and permits much more efficient homologation than can be achieved with diazomethane. © 1982, The Pharmaceutical Society of Japan. All rights reserved.