Hydrochloric Acid → 2-(4-Nitrophenyl)-1-(1-propylimidazol-2-yl)ethanone

Beteiligte Stoffe

Reaktionsschritte

To a solution of 1-propylimidazole (13.5 g) in dry tetrahydrofuran (200 ml) was added dropwise n-butyllithium (1.6 m hexane solution, 91.9 ml) under argon atmosphere at −78° C.,. The mixture as it is was stirred for 30 minutes, and added dropwise to a solution of N-methoxy-N-methyl-2-(4-nitrophenyl)acetoamide (27.5 g) in dry tetrahydrofuran (300 ml) under argon atmosphere at −78° C.,. The mixture was allowed to be at room temperature and stirred overnight, and 6N hydrochloric acid (30 ml.) was added to the mixture at 0° C. The mixture was neutralized with potassium carbonate, extracted with ethyl acetate, washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by basic silica gel column chromatography (hexane:ethyl acetate=2:1). The obtained solid was washed with hexane-diisopropyl ether to give 2-(4-nitrophenyl)-1-(1-propylimidazol-2-yl)ethanone (1.25 g) as red crystals.

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