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Application of microwave heating technique for rapid synthesis of ?,?-unsaturated esters

Srikrishna, Adusumilli and Sankuratri, Nagaraju and Kondaiah, Paturu (1995) Application of microwave heating technique for rapid synthesis of ?,?-unsaturated esters. In: Tetrahedron, 51 (6). pp. 1809-1816.

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Official URL: http://dx.doi.org/10.1016/0040-4020(94)01058-8


The use of microwave heating technique for the acceleration of ortho ester Claisen rearrangement (a three step transformation) is described. Irradiation of a DMF solution of the allyl alcohol 5, triethyl orthoacetate and propionic acid (catalytic) in an Erlenmeyer flask for 10 minutes in a microwave oven generated the ester 8 in 83% yield. Analogously, ortho ester Claisen rearrangement of a variety of allyl and propargyl alcohols (9, 12-22) were achieved. The formation of the diester 10 from 2-butyne-1,4-diol (9) via the ortho ester Claisen rearrangement of two allyl alcohol moieties (involving sh steps) in 15 minutes, demonstrates the versatility of the microwave heating technique.

Item Type: Journal Article
Publication: Tetrahedron
Publisher: Elsevier Science
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Biological Sciences > Molecular Reproduction, Development & Genetics
Division of Chemical Sciences > Organic Chemistry
Date Deposited: 26 Apr 2011 06:15
Last Modified: 02 Nov 2011 06:33
URI: http://eprints.iisc.ac.in/id/eprint/36926

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