Imidazole → HCID 90424727, compound

Participants

Reaction Steps

Add 1H-imidazole (19.72 g; 6.2 equiv; 289.67 mmoles) followed by tert-butylchlorodiphenylsilane (12.00 mL; 1.0 equiv; 46.28 mmoles) to a solution of freshly distilled glycidol (5.0 mL; 1.62 equiv; 75.05 mmoles) in acetonitrile (50 mL). Stir the solution at ambient temperature for 30 minutes, then heat to reflux for 4 hours. Allow the mixture to cool to ambient temperature and concentrate the reaction mixture, then pour the residue into dichloromethane/2M sodium bicarbonate (1:1, 400 mL). Separate the layers and further extract the aqueous layer with dichloromethane (2×). Dry the combined organic extracts over magnesium sulfate, filter, and concentrate to afford crude product. Purification by column chromatography affords the desired 1-[tert-butyl(diphenyl)silyl]oxy-3-imidazol-1-yl-propan-2-ol (8.87 g; 50%). MS (m/z): 381(M+1).

Provenance & Evidence