The Journal of organic chemistry

[1, 2]-Anionic Rearrangement of 2-Benzyloxypyridine and Related Pyridyl Ethers

J Yang, GB Dudley

Index: Yang, Jingyue; Dudley, Gregory B. Journal of Organic Chemistry, 2009 , vol. 74, # 20 p. 7998 - 8000

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Citation Number: 14

Abstract

An anionic rearrangement of 2-benzyloxypyridine is described. Pyridine-directed metalation of the benzylic carbon leads to 1, 2-migration of pyridine via a postulated associative mechanism (addition/elimination). Several aryl pyridyl carbinols were obtained in high yields. A formal synthesis of carbinoxamine, an antihistamine drug used for the treatment of seasonal allergies and hay fever, emerges from this methodology.