ZnI 2 -Mediated Cyanomethyl Ether Synthesis from MEM Ethers with Trimethylsilyl Cyanide

A highly practical protocol for preparing cyanomethyl ethers from aliphatic alcohols via their MEM ethers has been developed using trimethylsilyl cyanide in the presence of a Lewis acid. A number of Lewis acids were investigated, and ZnI 2 was found to be the most effective for converting a variety of MEM ethers to the corresponding cyanomethyl ethers. Both bidentate coordination of ZnI 2 with the MEM group and steric hindrance of the substrates play pivotal roles in this transformation.