Next Article in Journal
Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation
Previous Article in Journal
Facile Microwave-assisted Synthesis of 9,10-Dihydro-9,10-ethanoanthracene-11-carboxylic acid Methyl Ester
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
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 / Revised: 22 September 2005 / Accepted: 23 September 2005 / Published: 30 November 2005
View Full-Text   |   Download PDF [54 KB, uploaded 18 June 2014]   |  

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 (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert