A simple route to synthesize (E)-3 propyl-4-oxo-2-butenoic acid esters through the Z isomer
Articolo
Data di Pubblicazione:
2018
Citazione:
A simple route to synthesize (E)-3 propyl-4-oxo-2-butenoic acid esters through the Z isomer / C. Bolchi, G. Roda, M. Pallavicini. - In: SYNTHETIC COMMUNICATIONS. - ISSN 0039-7911. - 48:1(2018), pp. 85-90. [10.1080/00397911.2017.1390587]
Abstract:
Esters of 3-alkyl-2-oxo-4-butenoic acid, which are very important synthons, are not equally accessible in both E and Z configuration. The Z isomers can be easily obtained from 3-alkyl-4-hydroxybutenolides, in turn prepared by aminoalkylation of aliphatic aldehydes with glyoxylic acid. The E isomers, on the contrary, result from laborious procedures: the condensation of aldehydes with glyoxylic acid, followed by separation from γ-hydroxybutenolide by-product and esterification, or of aldehydes enamines with glyoxylic esters, followed by Z ester by-product conversion into γ-aminobutenolide and purification. Here, we describe a straightforward route to the title compounds, applied to methyl (E)-3-propyl-4-oxo-2-butenoate, avoiding any problematic by-product or isomer chromatographic separation: pentanal and glyoxylic acid are condensed to 3-propyl-4-hydroxybutenolide, which is converted to methyl (Z)-3-propyl-4-oxo-2-butenoate and then isomerized to the E ester under acidic conditions.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
3-alkyl-4-hydroxybutenolide, 3-alkyl-4-oxobutenoic acid ester, 3-alkylbutenolide, e configuration, isomerization, z configuration
Elenco autori:
C. Bolchi, G. Roda, M. Pallavicini
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