Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester

A simple and efficient method for the preparation of 1-methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester (1) is described. The first step is a highly regioselective Diels-Alder reaction between 2-methylfuran and methyl-3-bromo-propiolate. A remarkably difficult ketal hydrolysi...

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Autores principales: Aragão, Valquiria, Constantino, Mauricio Gomes, Beatriz, Adilson, José da Silva, Gil Valdo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2005
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147635/
https://www.ncbi.nlm.nih.gov/pubmed/18007537
http://dx.doi.org/10.3390/10111413
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author Aragão, Valquiria
Constantino, Mauricio Gomes
Beatriz, Adilson
José da Silva, Gil Valdo
author_facet Aragão, Valquiria
Constantino, Mauricio Gomes
Beatriz, Adilson
José da Silva, Gil Valdo
author_sort Aragão, Valquiria
collection PubMed
description A simple and efficient method for the preparation of 1-methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester (1) is described. The first step is a highly regioselective Diels-Alder reaction between 2-methylfuran and methyl-3-bromo-propiolate. A remarkably difficult ketal hydrolysis reaction was effected by treatment with HCl, a simple reagent that was shown to be more efficient, in this case, than commonly used more elaborate methods.
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spelling pubmed-61476352018-11-19 Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester Aragão, Valquiria Constantino, Mauricio Gomes Beatriz, Adilson José da Silva, Gil Valdo Molecules Article A simple and efficient method for the preparation of 1-methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester (1) is described. The first step is a highly regioselective Diels-Alder reaction between 2-methylfuran and methyl-3-bromo-propiolate. A remarkably difficult ketal hydrolysis reaction was effected by treatment with HCl, a simple reagent that was shown to be more efficient, in this case, than commonly used more elaborate methods. MDPI 2005-11-30 /pmc/articles/PMC6147635/ /pubmed/18007537 http://dx.doi.org/10.3390/10111413 Text en © 2005 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Aragão, Valquiria
Constantino, Mauricio Gomes
Beatriz, Adilson
José da Silva, Gil Valdo
Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester
title Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester
title_full Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester
title_fullStr Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester
title_full_unstemmed Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester
title_short Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester
title_sort synthesis of 1-methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6147635/
https://www.ncbi.nlm.nih.gov/pubmed/18007537
http://dx.doi.org/10.3390/10111413
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