Potassium Hydride in Paraffin: A Useful Base for Organic Synthesis

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.