Molecules 2005, 10(11), 1413-1418; doi:10.3390/10111413

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

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 2 Departamento de Química, Centro de Ciências Exatas e Tecnologia, Universidade Federal de Mato Grosso do Sul, Avenida Senador Filinto Müller, 1555, 79070-90, Campo Grande, MS, Brazil
* Author to whom correspondence should be addressed.
Received: 25 August 2005; in revised form: 22 September 2005 / Accepted: 23 September 2005 / Published: 30 November 2005
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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.
Keywords: 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester; ketal hydrolysis; Diels-Alder reaction.

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MDPI and ACS Style

Aragao, V.; Constantino, M.G.; Beatriz, A.; José da Silva, G.V. Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester. Molecules 2005, 10, 1413-1418.

AMA Style

Aragao V, Constantino MG, Beatriz A, José da Silva GV. Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester. Molecules. 2005; 10(11):1413-1418.

Chicago/Turabian Style

Aragao, Valquiria; Constantino, Mauricio G.; Beatriz, Adilson; José da Silva, Gil V. 2005. "Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester." Molecules 10, no. 11: 1413-1418.

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