Hexamethylenetetramine-Mediated Transesterification of β-Keto Esters

Abstract

H e x a m e t h y l e n e t e t r a m i n e -M e d i a t e d T r a n s e s t e r i f i c a t i o n o f b -K e t o E s t e r s Abstract: Treatment of methyl or ethyl b-keto esters with primary, secondary, or tertiary alcohols in the presence of a catalytic amount of hexamethylenetetramine results in good to high yields of the corresponding esters.

Synthetic studies of β-ketoesters

“…In the course of our research on the application of βdicarbonyl compounds for the synthesis of heterocycles and carbocycles using multicomponent reactions [3,[11][12][13][14][15][16][17] , I needed to prepare chiral β-keto esters and found that currently existing methods were not wholly satisfactory. We report now the development of a modified synthetic procedure for the practical synthesis of acetoacetates 3 from 2, 2, 6-trimethyl-4H-1, 3-dioxin-4-one (1) and alcohols, including chiral alcohols, or primary or secondary amines under mild conditions that avoid side reactions and give essentially quantitative yields.…”