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Synthesis 1986; 1986(7): 552-554
DOI: 10.1055/s-1986-31698
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Dialkylation of Diesters

Ronald J. Weagley* , Harry W. Gibson
  • *Webster Research Center, Xerox Corporation, 800 Phillips Road W-114, Webster, New York 14580, U. S. A.
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Publication Date:
20 August 2002 (online)

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Dimethyl and diethyl 2,2,4,4-tetramethylglutarates have been synthesized in greater than 92% yield by lithium diisopropylamide promoted methylation of the ester enolates of 2,4-dimethyl- and 2,2-dimethyl-glutaric acids. 1, 3-Dimethoxycarbonyl-1,3-dimethylcyclopentane was prepared in 84% yield by dimethylation of the corresponding diester. The latter dialkylation occurs in one step using two equivalents of base followed by two equivalents of methyl iodide, while the former requires a two step procedure, introducing one methyl group at a time.