A useful variation of the Williamson synthesis involves silver oxide, Ag2O, as a mild base rather than NaH. Under these conditions, the free alcohol reacts directly with alkyl halide, so there is no need to preform the metal alkoxide intermediate. Sugars react particularly well; glucose, for example, reacts with excess iodomethane in the presence of Ag2O to generate a pentaether in 85% yield.
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