Removal of Triphenylphosphine Oxide by Precipitation with Zinc Chloride in Polar Solvents.

Autor: Batesky DC; Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States and., Goldfogel MJ; Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States., Weix DJ; Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2017 Oct 06; Vol. 82 (19), pp. 9931-9936. Date of Electronic Publication: 2017 Sep 28.
DOI: 10.1021/acs.joc.7b00459
Abstrakt: While the use of triphenylphosphine as a reductant is common in organic synthesis, the resulting triphenylphosphine oxide (TPPO) waste can be difficult to separate from the reaction product. While a number of strategies to precipitate TPPO are available, none have been reported to work in more polar solvents. We report here that mixing ZnCl 2 with TPPO precipitates a TPPO-Zn complex in high yield in several common polar organic solvents. The solvent compatibility of this procedure and the reliability of the precipitation in the presence of polar functional groups were examined to show the utility and limitations of this method.
Databáze: MEDLINE
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