Convenient method for preparing benzyl ethers and esters using 2-benzyloxypyridine

Abstract

2-Benzyloxy-1-methylpyridinium triflate (1) is emerging as a mild, convenient, and in some cases uniquely effective new reagent for the synthesis of benzyl ethers and esters. This article provides a revised benzyl transfer protocol in which N-methylation of 2-benzyloxypyridine delivers the active reagent in situ. Observations on the appropriate choice of solvent (toluene vs. trifluorotoluene) and the extension of this methodology to the synthesis of other arylmethyl ethers are included.

Keywords

• alcohols
• alkylation
• benzyl
• electrophilic substitution
• esters
• ethers
• protecting groups
• reagent