Tetrahydropyran → HCID 86694696, compound

Participants

Reaction Steps

To a solution of 4-ethyl-1H-benzo[d]imidazole-5-carbonitrile (6.8 g, 0.04 mol) in dry toluene (70 mL) was added tetrahydro-2H-pyran (10.53 g, 0.12 mol, 3 equiv.) and pyridinium-p-toluenesulfonate (4 g, 0.02 mol, 0.5 equiv.) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was concentrated, quenched with water and extracted with EtOAc. The combined organic layers were washed with brine and then dried (Na2SO4), filtered, and concentrated. The crude product was purified by SiO2 chromatography eluting with 50% EtOAc/hexane to afford 4-ethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbonitrile (7 g, 69% yield) as a yellow oil.

Provenance & Evidence