Synthesis of 1-methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Valquiria Aragão; Mauricio Gomes Constantino; Adilson Beatriz; Gil Valdo José da Silva

doi:10.3390/10111413

Synthesis of 1-methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

Molecules. 2005 Nov 30;10(11):1413-8. doi: 10.3390/10111413.

Authors

Valquiria Aragão¹, Mauricio Gomes Constantino, Adilson Beatriz, Gil Valdo José da Silva

Affiliation

¹ Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida dos Bandeirantes, 3900, 14040-901, Ribeirão Preto, SP, Brazil. varagao@usp.br

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry*
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Carboxylic Acids / chemistry*
Catalysis
Esters / chemical synthesis*
Esters / chemistry
Hydrolysis
Molecular Structure
Stereoisomerism

Substances

1-methyl-3-oxo-7-oxabicyclo(2.2.1)hept-5-ene-2-carboxylic acid methyl ester
Bridged Bicyclo Compounds
Bridged Bicyclo Compounds, Heterocyclic
Carboxylic Acids
Esters