دورية أكاديمية
A simple route to synthesize (E)-3 propyl-4-oxo-2-butenoic acid esters through the Z isomer
| العنوان: | A simple route to synthesize (E)-3 propyl-4-oxo-2-butenoic acid esters through the Z isomer |
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| المؤلفون: | C. Bolchi, G. Roda, M. Pallavicini |
| المساهمون: | C. Bolchi, G. Roda, M. Pallavicini |
| بيانات النشر: | Taylor & Francis |
| سنة النشر: | 2018 |
| المجموعة: | The University of Milan: Archivio Istituzionale della Ricerca (AIR) |
| مصطلحات موضوعية: | 3-alkyl-4-hydroxybutenolide, 3-alkyl-4-oxobutenoic acid ester, 3-alkylbutenolide, e configuration, isomerization, z configuration, Settore CHIM/08 - Chimica Farmaceutica |
| الوصف: | 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. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| العلاقة: | info:eu-repo/semantics/altIdentifier/wos/WOS:000426954000010; volume:48; issue:1; firstpage:85; lastpage:90; numberofpages:6; journal:SYNTHETIC COMMUNICATIONS; http://hdl.handle.net/2434/532297Test; info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85038117618 |
| DOI: | 10.1080/00397911.2017.1390587 |
| الإتاحة: | https://doi.org/10.1080/00397911.2017.1390587Test http://hdl.handle.net/2434/532297Test |
| حقوق: | info:eu-repo/semantics/closedAccess |
| رقم الانضمام: | edsbas.E4F47C10 |
| قاعدة البيانات: | BASE |
| DOI: | 10.1080/00397911.2017.1390587 |
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