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CHLORAL HYDRATE AS A WATER CARRIER FOR THE EFFICIENT DEPROTECTION OF ACETALS, DITHIOACETALS, AND TETRAHYDROPYRANYL ETHERS IN ORGANIC SOLVENTS

Chandrasekhar, Sosale and Shrinidhi, Annadka (2014) CHLORAL HYDRATE AS A WATER CARRIER FOR THE EFFICIENT DEPROTECTION OF ACETALS, DITHIOACETALS, AND TETRAHYDROPYRANYL ETHERS IN ORGANIC SOLVENTS. In: SYNTHETIC COMMUNICATIONS, 44 (13). pp. 1904-1913.

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Official URL: http://dx.doi.org/10.1080/00397911.2013.876652

Abstract

The efficient deprotection of several acetals, dithioacetals, and tetrahydropyranyl (THP) ethers under ambient conditions, using chloral hydrate in hexane, is described. Excellent yields were realized for a wide range of both aliphatic and aromatic substrates. The method is characterized by mild conditions (room temperatures or below), simple workup, and the ready availability of chloral hydrate. High chemoselectivity was also observed in the deprotection, acetonides, esters, and amides being unaffected under the reaction conditions. Products were generally purified chromatographically and identified spectrally. These results constitute a novel addition to current methodology involving a widely employed deprotection tactic in organic synthesis. It seems likely that the mechanism of the reaction involves adsorption of the substrate on the surface of the sparingly soluble chloral hydrate.

Item Type: Journal Article
Additional Information: copyright for this article belongs to TAYLOR & FRANCIS INC, 530 CHESTNUT STREET, STE 850, PHILADELPHIA, PA 19106 USA
Keywords: Acetals; chemoselective; deprotection; hydrolysis; nonaqueous
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 19 Aug 2014 09:23
Last Modified: 19 Aug 2014 09:23
URI: http://eprints.iisc.ac.in/id/eprint/49575

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