Water → HCID 67286575, compound

Participants

Reaction Steps

To a stirred suspension of 1H-benzoimidazol-4-ol (440 mg, 3.28 mmol) in THF (13 mL) at room temperature was added NaH (60% dispersion in mineral oil; 276 mg, 6.89 mmol) in 3 portions over 15 min. The mixture was stirred at room temperature for 1.5 hours before it was heated to 65° C. for 30 min. The THF was removed and replaced with DMF (10 mL) and the mixture was warmed to 65° C. for 30 min. The mixture was cooled to 10° C., 2-(trimethylsilyl)ethoxymethyl chloride (1.19 mL, 6.72 mmol) was added dropwise and the mixture was stirred at room temperature overnight. H2O and Et2O were added, the mixture was filtered and the phases separated. The aqueous phase was extracted into Et2O (×3), dried (MgSO4) and concentrated in vacuo. The product was purified by SiO2 chromatography and followed by trituration with Et2O to provide the title compound (177 mg).

Provenance & Evidence