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Synthesis 1989; 1989(3): 163-166
DOI: 10.1055/s-1989-27182
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The Synthesis of O-Silyl Ketene Acetals from α-Haloesters

William J. Schulz, Jr.* , John L. Speier
  • *Dow Corning Corporation, Specialty Intermediates and Chemicals Research, Midland, MI 48686, USA
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Publication Date:
17 September 2002 (online)

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α-Haloesters of the general structure R1R2CXCO2R3 1 have been shown to react with sodium in the presence of a halosilane 2 to yield the corresponding O-silyl ketene acetals 3 (SKAs) according to equation 4. The factor that most influences the yields in these reactions is the concentration of halosilane; if there is a deficiency of halosilane, then acyloin condensation products will detract from the yield of SKAs. The reaction is quite general, and often gives yields in excess of 90 % of the desired SKA(s).

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