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

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

1,* , 1, 2 and 1
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. 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester; ketal hydrolysis; Diels-Alder reaction.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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