One-Pot Synthesis of β-Keto Esters and Preparation of 3-Ketopalmitoyl-CoA

被引：2

作者：

Kosak, Urban ^{[1
]}

Kovac, Andreja ^{[1
]}

Gobec, Stanislav ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Pharm, Ljubljana 1000, Slovenia

来源：

SYNLETT | 2012年 / 11期

关键词：

beta-keto esters; one-pot reaction; deacetylation; 3-ketopalmitoyl coenzyme A; 17 beta-hydroxysteroid dehydrogenase type 12; COENZYME-A; ACIDS; CHLORIDE;

D O I：

10.1055/s-0031-1291149

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Keto esters were synthesized from acyl chlorides and sodium ethyl acetoacetate in EtOH using a simple 'one-pot, one-step' method. The deacetylation of alpha-acetyl beta-keto ester to beta-keto ester was performed simply, by heating the reaction mixture at reflux for 12 hours, without the addition of additional reagents (e. g., NH4Cl, NH3, MeOH, or NaOH). One of the beta-keto esters prepared using this method was ethyl 3-oxohexadecanoate, a key intermediate in the synthesis of 3-ketopalmitoyl coenzyme A (3-oxohexadecanoyl coenzyme A), a potential substrate of the biologically important enzyme 17 beta-hydroxysteroid dehydrogenase type 12.

引用

页码：1609 / 1612

页数：4