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  Home > JCE Print > Journal of Chemical Education > Issues > 1996  > October  >
In the Laboratory
A Convenient Synthesis of the Tetrasubstituted Pyrrole: An Undergraduate Heterocyclic Laboratory Experiment
Patrik Kolar, Miha Tisler
Department of Organic Chemistry, University of Ljubljana, SLO-1000 Ljubljana, Slovenia
Cover
October 1996
Vol. 73 No. 10
p. 986
Abstract
A two-step synthesis of tetrasubstituted pyrroles from esters of a-amino acids has been applied as a simple undergraduate laboratory experiment, which illustrates the utility of amino acids in heterocyclic synthesis. The enamine, prepared by an addition of L-phenylalanine ethyl ester to dimethyl acetylenedicarboxylate was cyclized in presence of sodium methoxide in methanol giving 5-benzyl-4-hydroxy-2,3-di(methoxycarbonyl)pyrrole in 63-72 % yield. The procedure represents an alternative to classical pyrrole syntheses which are usually included in practical undergraduate organic chemistry.
More Information
*  Citation
 Kolar, Patrik; Tisler, Miha. J. Chem. Educ. 1996 73 986.
*  Keywords
 Organic Chemistry
*  History
 Created:
Last Updated:		 September 22, 1999
February 21, 2006
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