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Evaluating a Sodium Dispersion Reagent for the Bouveault-Blanc Reduction of Esters

Jie An, D. Neil Work, Craig Kenyon and David J. Procter*

*School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, United Kingdom, Email: david.j.proctermanchester.ac.uk

J. An, D. N. Work, C. Kenyon, D. J. Procter, J. Org. Chem., 2014, 79, 6743-6747.

DOI: 10.1021/jo501093g (free Supporting Information)


Abstract

Na-D15, a sodium dispersion reagent with sodium particle size of 5-15 μm, is a nonpyrophoric reagent that can be handled in air. A broad range of aliphatic ester substrates were reduced to primary alcohols by Na-D15/i-PrOH with good yields. The method compares favorably with modern metal hydride reductions and is much safer and efficient than the traditional Bouveault-Blanc reduction.

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Key Words

Bouveault-Blanc reduction, Sodium


ID: J42-Y2014