Silica-Bound 3-{2-[Poly(ethylene Glycol)]ethyl}-Substituted 1-Methyl-1 H-imidazol-3-ium Bromide: A Recoverable Phase-Transfer Catalyst for Smooth and Regioselective Conversion of Oxiranes to β-Hydroxynitriles in Water.

A series of β-hydroxynitriles were efficiently synthesized from the regioselective ring opening of oxiranes by cyanide anion in the presence of silica-bound 3-{2-[poly(ethylene glycol)]ethyl}-substituted 1-methyl-1 H-imidazol-3-ium bromide (SiO2PEGImBr) as a novel recoverable phase-transfer catalyst in H2O ( Scheme 1 and Table 2). The workup procedure was straightforward, and the catalyst could be reused over four times with almost no loss of catalytic activity and selectivity. [ABSTRACT FROM AUTHOR]