Solid–liquid phase alkylation of P=O–functionalized CH acidic compounds utilizing phase transfer catalysis and microwave irradiation

Optimum conditions for the solid–liquid phase alkylation of methylenebis(diphenylphosphine oxide) (MBDPPO) and ethyl cyanomethylphosphonate (ECMP) were explored studying the role of phase transfer catalysis and microwave (MW) irradiation, as well as the effect of the cation of the alkali carbonate. It was found that the alkylation of MBDPPO may be best accomplished in acetonitrile, in the presence of a quaternary ammonium salt and Cs₂CO₃, while that of ECMP in the absence of catalyst and solvent using K₂CO₃. MW irradiation was beneficial in both cases. During the alkylation of ECMP, by‐products coming from the alcoholysis of the diethyl ester were also identified. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:174–179, 2011; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.20673