Imidazole → HCID 22244044, compound

Participants

Reaction Steps

tert-Butylchlorodiphenylsilane (8.86 ml, 34 mmol) was added slowly via syringe to a solution of (2,3,4-trifluorophenyl)methanol (5.0 g, 31 mmol) and imidazole (2.53 g, 37.2 mmol) in CH2Cl2 (30 ml) cooled in an ice water bath. The mixture warmed to room temperature and stir overnight. Solvent was removed and the residue was partitioned between Et2O and water. The Et2O was separated and washed with brine, and the combined aqueous layers were twice more extracted with Et2O, which was washed with brine. Drying (MgSO4) and removal of solvent gave an oil that was chromatographed on silica gel (50% CH2Cl2 in hexanes followed by gradient elution to 100% CH2Cl2) to isolate an oil that slowly solidified to afford 11.9 g (96%) of a white solid.

Provenance & Evidence