Tetrahedron

Lithiomethyl ethyl ether from chloromethyl ethyl ether via a DTBB-catalysed lithiation

A Guijarro, B Mancheño, J Ortiz, M Yus

Index: Guijarro, Albert; Mancheno, Balbino; Ortiz, Javier; Yus, Miguel Tetrahedron, 1996 , vol. 52, # 5 p. 1643 - 1650

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Citation Number: 16

Abstract

The reaction of equimolecular amounts of chloromethyl ethyl ether (1) and a carbonyl compound [BunCHO, ButCHO, PhCHO, Pri2CO, But2CO,(CH2) 4CO, 2-cyclohexenone, PhCOMe] with an excess of lithium powder (1: 7 molar ratio) and a catalytic amount of DTBB (5 mol%) in THF at 0° C (Method A) leads, after hydrolysis, to the corresponding hydroxyethers 2. The reaction can be also carried out in a two-step process: tandem ...