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|Type:||Artigo de periódico|
|Title:||Knoevenagel Condensation of Aromatic Aldehydes with Ethyl 4-Chloro-3-oxobutanoate in Ionic Liquids|
|Author:||de Paula, BRS|
|Abstract:||Knoevenagel condensations of aromatic aldehydes with ethyl 4-chloro-3-oxobutanoate catalyzed by morpholine/acetic acid were carried out in ionic liquids to give ethyl 2-chloroacetyl-3-arylpropenoates in 44-84% yield after 0.5 to 2 h at room temperature (25-28 degrees C). These conditions represent a greener protocol for the Knoevenagel condensation than those using refluxing benzene or toluene as solvent. Aromatic aldehydes having aryl groups 4-chlorophenyl, 4-methoxyphenyl, 2-thiofuranyl, 2-furanyl, phenyl and 3,4-methylenedioxyphenyl gave (E)/(Z) diastereomeric ratios of products from 56/44 to 85/15. The two isomers of each compound were separately isolated and characterized. The structure of the (E)-isomer of ethyl 2-chloroacetyl-3-(3',4' methylenedioxyphenyl) propenoate was determined by X-ray crystallography and an unequivocal methodology of (E)/(Z)-structural analysis by C-13 NMR (nuclear magnetic resonance) is presented.|
|Editor:||Soc Brasileira Quimica|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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