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Synthesis 1990; 1990(6): 495-496
DOI: 10.1055/s-1990-26917
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A Convenient One-Pot Method for the Hydroxymethylation of Grignard Reagents

C. A. Ogle* , T. E. Wilson, J. A. Stowe
  • *Department of Chemistry, University of North Carolina at Charlotte, Charlotte, NC-28223, USA
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Publication Date:
17 September 2002 (online)

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Grignard reagents and alkynyllithiums can be hydroxymethylated in a two-step one-pot reaction by reaction of a Grignard reagent with 1-chloro-2-(chloromethoxy)ethane (1), followed by treatment with sodium-potassium alloy and aqueous workup. The reaction was found to work for primary, secondary, tertiary, benzylic, allylic and aryl Grignard reagents in yields ranging from 57-95%.