Synthesis of 1-methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester |
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Authors: | Aragão Valquiria Constantino Mauricio Gomes Beatriz Adilson José da Silva Gil Valdo |
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Institution: | Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeir?o Preto, Universidade de S?o Paulo, Avenida dos Bandeirantes, 3900, 14040-901, Ribeir?o Preto, SP, Brazil. varagao@usp.br |
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Abstract: | A simple and efficient method for the preparation of 1-methyl-3-oxo-7- oxabicyclo2.2.1]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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