Preparatively Useful Method for the Synthesis of Diels-Alder Adducts between Furan and Methyl Acrylate
- 1 November 1984
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 57 (11) , 3339-3340
- https://doi.org/10.1246/bcsj.57.3339
Abstract
The Diels-Alder adducts of furan with methyl acrylate were successfully prepared by two methods on a preparative scale. The BF3·OEt2-catalyzed reaction of furan with methyl acrylate gave a 7:3 mixture of endo and exo adducts in 75.7% yield. When acryloyl chloride was used as a dienophile, after esterification with methanol, a 3:7 mixture of the same adducts was obtained in 76.5% overall yield.Keywords
This publication has 10 references indexed in Scilit:
- Intramolecular diels-alder reaction with furan diene. A new synthesis of 11-keto steroidsTetrahedron Letters, 1983
- The Preparation of Optically Pure 7‐Oxabicyclo [2.2.1]hept‐2‐ene Derivatives. The CD Spectrum of (+)‐(1R)‐7‐Oxabicyclo [2.2.1]hept‐5‐en‐2‐oneHelvetica Chimica Acta, 1983
- Catalyzed addition of furan with acrylic monomersThe Journal of Organic Chemistry, 1983
- Total synthesis of the hypocholesterolemic agent (+)-compactinJournal of the American Chemical Society, 1983
- Brief diels alder syntheses of (±)-methyl 5-epishikimate and (±)-methyl -3,4-dihydro-3,4-dihydroxybenzoate.Tetrahedron Letters, 1983
- Copper(I)‐ and Copper(II)‐catalyzed Diels‐Alder Additions of α‐Substituted Acrylonitrile to Furan. The Synthesis of 7‐Oxa‐bicyclo[2.2.1]hept‐5‐en‐2‐oneHelvetica Chimica Acta, 1982
- High Pressure Organic Chemistry. V. Diels-Alder Reactions of Furan with Acrylic and Maleic EstersBulletin of the Chemical Society of Japan, 1982
- On the lewis acid catalyzed diels-alder reaction of furan. regio- and stereospecific synthesis of substituted cyclohexenols and cyclohexadienols.Tetrahedron Letters, 1982
- High-pressure Diels-Alder Reactions of Furans with a-Chiloro- and a-AcetoxyacrylonitrileHETEROCYCLES, 1981
- Polymerizable Esters of Lactic Acid. α-Carbalkoxyethyl Acrylates and MethacrylatesJournal of the American Chemical Society, 1945