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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Abstract

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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