Elsevier

Tetrahedron Letters

Volume 39, Issue 50, 10 December 1998, Pages 9287-9288
Tetrahedron Letters

Mild and efficient tetrahydropyranylation of alcohols-catalysis by lithium perchlorate in diethyl ether

https://doi.org/10.1016/S0040-4039(98)02087-5Get rights and content

Abstract

Treatment of 3,4-dihydro-2H-pyran 1 with various alcohols 2 – 10 furnished the tetrahydropyranyl ethers 11 – 19 in the presence of 5M lithium perchlorate in diethyl ether (5M LPDE), which is essentially a neutral medium.

Treatment of 3,4-dihydropyran 1 with various alcohols 2 – 9 furnished the tetrahydropyranyl ethers 10–17 in the

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  • N,N′-Dibromo-N,N′-1,2-ethanediylbis(benzene sulfonamide) as a novel N-bromo reagent catalyzed tetrahydropyranylation/depyranylation of alcohols and phenols under mild conditions

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    There are several known methods for the tetrahydropyranylation and depyranylation of alcohols [3]. The most commonly used reagents that can catalyze the protection and deportection of both transformations are p-toluenesulfonic acid (PTSA) [4,5], pyridinium p-toluenesulfonate (PPTS) [6], NH4Cl [7], acetonyltriphenylphosphonium bromide [8], I2[9,10], LiBr [11], ZrCl4[12], tetrabutylammonium tribromide [13], Fe(ClO4)3[14], K5CoW12O40 · 3H2O [15], PdCl2(CH3CN)2[16], trichloroisocyanuric acid [17], silica sulfuric acid [18], Bi(NO3)3 · 5H2O [19], aqueous zinc tetrafluoroborate [20], and AlCl3 · 6H2O [21]. However, in most cases these procedures suffer from one or more disadvantages such as stringent conditions, elevated reaction temperatures, longer reaction times, and expensive reagents.

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