[Synthesis]
Synthesis of 1-propyl-1H-imidazole: Sodium hydride (55%, 0.966 g, 22.1 mmol) was slowly added to a solution of tetrahydrofuran (50.0 mL) of imidazole (1.37 g, 20.1 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 hour. Subsequently, 1-bromopropane (5.48 mL, 60.3 mmol) was added dropwise at the same temperature and the reaction solution was continued to be stirred for 16 hours. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and the filter cake was washed with tetrahydrofuran. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by fast column chromatography (silica gel as stationary phase and chloroform/methanol as eluent) to afford 1-propyl-1H-imidazole (2.07 g, 18.8 mmol, 93% yield) as a colorless oil.1H NMR (400 MHz, CDCl3) δ: 0.93 (3H, t, J = 7.2 Hz), 1.81 (2H, td, J = 7.2, 14.4 Hz), 3.90 (2H, t, J = 7.2 Hz), 6.91 (1H, s), 7.06 (1H, s), 7.46 (1H, s). |