HCID 67026311, compound → HCID 67026311, compound

Participants

Reaction Steps

1-(5-Methyl-1-trityl-1H-imidazolyl)-1-(naphthalen-1-yl)ethanol and 1-(4-methyl-1-trityl-1H-imidazol-5-yl)-1-(naphthalen-1-yl)ethanol (12): A solution of (11) (1.33 g, 2.78 mmol) in dichloromethane (50 mL) at 0° C. was added methyl magnesium bromide (3.0 M in diethyl ether, 1.85 mL, 5.50 mmol) drop wise. The reaction mixture was warmed to room temperature over night. The mixture was quenched with ammonium chloride (aq). The resulting aqueous layer was extracted with chloroform three times (200 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 50% hexane and 50% ethyl acetate to give 1-(5-methyl-1-trityl-1H-imidazol-4-yl)-1-(naphthalen-1-yl)ethanol and 1-(4-methyl-1-trityl-1H-imidazol-5-yl)-1-(naphthalen-1-yl)ethanol (12) (1.21 g, 2.45 mmol, 88% yield).

Provenance & Evidence