Ammonium Chloride → 6-(hydroxy(1-trityl-1H-imidazol-4-yl)methyl)-N-methyl-2-naphthamide

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 6-bromo-N-methyl-2-naphthamide (1.0 g, 3.79 mmol) was added to tetrahydrofuran (25 mL), and then 1.0 mol/L dibutylmagnesium heptane solution (2.0 mL) was added dropwise thereto at room temperature. The obtained solution was cooled to −13° C., 1.6 mol/L n-butyllithium hexane solution (2.6 mL) was added dropwise thereto, and the mixture was stirred at the same temperature for 1.5 hr. A solution of 1-trityl-4-formyl-1H-imidazole (1.4 g, 4.2 mmol) in tetrahydrofuran (15 mL) was added dropwise to the reaction mixture at −11° C., and the mixture was stirred at the same temperature for 5 hr. The reaction mixture was allowed to warm to 6° C. over 2.5 hr, and 20 w/v % aqueous ammonium chloride solution (30 mL) was added dropwise thereto. The organic layer was separated, and quantified to give 6-[hydroxy(1-trityl-1H-imidazol-4-yl)methyl]-N-methyl-2-naphthamide (1.2 g, 2.24 mmol). yield 71%.

Provenance & Evidence