Synthetic Communications®

Sodium Borohydride–Mediated Transesterification

G Sereda, S Pothula, J Dreessen

Index: Sereda, Grigoriy; Pothula, Swetha; Dreessen, James Synthetic Communications, 2010 , vol. 40, # 9 p. 1312 - 1321

Full Text: HTML

Citation Number: 4

Abstract

In the presence of sodium borohydride, esters react with alcohols with formation of the corresponding esters. The reaction is sensitive to the solvent, structure of the ester, and is often concurrent with reduction. Thioesters containing an ester group can be selectively cleaved by the reagent. Both esters and thioesters attached to solid support are resistant toward sodium borohydride. The in situ prepared sodium tetraalkoxyborate is introduced ...