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

Molecules

Valquiria Aragão²  Mauricio Gomes Constantino²  Adilson Beatriz¹ 

[1] 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;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 Tel. [phone]; Fax [phone]

关键词: 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid methyl ester;    ketal hydrolysis;    Diels-Alder reaction;   

DOI  :  10.3390/10111413

来源: mdpi

【 摘 要 】

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.

【 授权许可】

Unknown   
© 2005 by MDPI (http://www.mdpi.org).