Imidazole → HCID 123241194, compound

Participants

Reaction Steps

Add 1H-imidazole (14.70 g; 4 equiv; 215.99 mmoles) followed by tert-butylchlorodiphenylsilane (14.00 mL; 1.0 equiv; 54.00 mmoles) to a 0° C. solution of freshly distilled (S)-glycidol (3.66 mL; 1.0 equiv; 54.00 mmoles) in acetonitrile (40 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 and 2M sodium bicarbonate solution (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 (2R)-1-[tert-butyl(diphenyl)silyl]oxy-3-imidazol-1-yl-propan-2-ol (9.25 g; 45%). MS (m/z): 381(M+1).

Provenance & Evidence