Ammonium Chloride → (6-ethoxynaphthalen-2-yl)(1-trityl-1H-imidazol-4-yl)methanol

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Reaction Steps

2-Bromo-6-ethoxynaphthalene (5.3 g) was dissolved in THF (40 ml) and magnesium (0.515 g) and methyl iodide (one drop) were added and the mixture was vigorously stirred to dissolve magnesium. The reaction mixture was ice-cooled and a solution of 4-formyl-1-tritylimidazole (7 g) in THF (80 ml) was added dropwise over 30 min. The mixture was stirred at room temperature for 1 h. To the reaction mixture were added saturated aqueous solution (40 ml) of ammonium chloride and water (40 ml) and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate and concentrated. The residue was washed with ethyl acetate to give (6-ethoxynaphthalen-2-yl)-(1-trityl-1H-imidazol-4-yl)methanol (6.3 g) as a colorless powder. This product (6.3 g) was dissolved in dichloromethane (120 ml) and manganese dioxide (6 g) was added. The mixture was stirred at room temperature overnight. The reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was crystallized from THF-ethyl acetate to give the title compound (5.5 g) as a colorless powder.

Provenance & Evidence