4.7 Article

Potassium hydride in paraffin: A useful base for organic synthesis

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 23, Pages 8973-8974

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo061420v

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Funding

  1. NIGMS NIH HHS [R01 GM060287, R01 GM060287-01, GM 60287] Funding Source: Medline

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The preparation of potassium hydride as a 1:1 homogenate with paraffin, termed KH(P), is reported. KH(P), a solid at room temperature, is stable without special handling. On suspension in THF with a phosphonium salt, KH(P) rapidly generates the ylide. Wittig condensation with aromatic, aliphatic, and alpha,beta-unsaturated aldehydes proceeds with high Z selectivity. KH(P) should be a generally useful base for organic synthesis.

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