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Synthesis 1985; 1985(10): 941-943
DOI: 10.1055/s-1985-31393
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Convenient Synthesis of Ethyl Triethylsilyldiazoacetate and Stereoselective Preparation of Aliphatic Silylketene Acetals: In situ Formation of Triethylsilyl Perchlorate

Craig S. Wilcox* , Robert E. Babston
  • *Department of Chemistry, University of Texas at Austin, Austin, Texas 78 712, U.S.A.
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Publication Date:
27 September 2002 (online)

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Experimental details are reported for the silylation of esters by a method based upon in situ preparation of triethylsilyl perchlorate. The preparation of ethyl triethylsilyldiazoacetate (5) in 99% yield from ethyl diazoacetate (3) is detailed. A preparative procedure for the stereoselective formation of a (Z)-O-silylketene acetal 2b from isopropyl propanoate (1) is described.

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