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One-Pot in Situ Formation and Reaction of Trimethyl(trichloromethyl)silane: Application to the Synthesis of 2,2,2-Trichloromethylcarbinols

Kevin E. Henegar* and Ricardo Lira

*Pfizer Global Research and Development, Groton Laboratories Eastern Point Road, Groton, Connecticut 06340, United States, Email:

K. E. Henegar, R. Lira, J. Org. Chem., 2012, 77, 2999-3004.

DOI: 10.1021/jo202588j


A scalable procedure for the synthesis of TMS-protected-2,2,2-trichloromethylcarbinols and 2,2,2-trichloromethylcarbinols employs an in situ generation and reaction of trimethyl(trichloromethyl)silane (CCl3-TMS). The procedure avoids the exposure of the carbonyl compounds to the strongly basic conditions typically used for this transformation and also avoids isolation of the difficult-to-handle CCl3-TMS.

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ID: J42-Y2012-0840