Preparation of beta-keto esters and beta-diketones by C-acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles.

Acyl-, aroyl-, and heteroaroyl-acetic esters 6a-f and 8a-l are prepared by reactions of 1-acylbenzotriazoles 1a-k with acetoacetic esters 5 or 7a,b in the presence of sodium hydride followed by regioselective deacetylation. Similar C-acylation/deacetylation of acetylacetone and benzoylacetone affords beta-diketones 10a-d and 13a-c, respectively. Copyright 2004 American Chemical Society