AN EFFICIENT SYNTHETIC PROTOCOL FOR THE TETRAHYDROPYRANYLATION OF ALCOHOLS AND PHENOLS CATALYZED BY MAGNESIUM CHLORIDE

Abstract

Hydroxyl group is a key functional moiety of many biologically important natural and unnatural compounds. Protection and deprotection of hydroxyl group during the synthesis is a very common strategy followed to synthesize compounds chemo selectively. Hydroxyl group is usually protected as tetrahydropyranyl (THP) ether because of its low cost, ease of preparation and stability of THP ethers towards metal hydrides and acylating, alkylating, Grignard and organometallic reagents. Thus there is a need to develop much simpler methodologies for the synthesis of tetrahydropyranyl ethers. Synthesis of tetrahydropyranyl ethers from the reaction of various phenols and alcohols using magnesium (II) chloride as a novel catalyst is described. This methodology proved to be very efficient with different phenols and alcohols at room temperature to afford the products in reasonable yields without noticeable side reactions. All the products are characterized completely based on IR, NMR and GC-MS spectral analy