Deblocking of ω-Chloralkyl Esters with Sodium Sulfide

Abstract

One of our current research programs is concerned with functional group protection. We reported some time ago, the synthesis of methylthiomethyl esters and their solvelytic behavior.^1,2 These esters can be hydrolyzed under mild, nonbasic conditions, and are transformable into other esters and amides in good yields. We now wish to point out that 4-chlorobutyl and 5-chloropentyl esters may be cleaved by sodium sulfide.