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Synlett 2012; 23(11): 1609-1612
DOI: 10.1055/s-0031-1291149
DOI: 10.1055/s-0031-1291149
letter
One-Pot Synthesis of β-Keto Esters and Preparation of 3-Ketopalmitoyl-CoA
Further Information
Publication History
Received: 29 February 2012
Accepted after revision: 10 April 2012
Publication Date:
13 June 2012 (online)
Abstract
β-Keto esters were synthesized from acyl chlorides and sodium ethyl acetoacetate in EtOH using a simple ‘one-pot, one-step’ method. The deacetylation of α-acetyl β-keto ester to β-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 β-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 17β-hydroxysteroid dehydrogenase type 12.
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