Imidazole → 1-(18-(benzyloxy)octadecan-9-yl)-1H-imidazole

Participants

Reaction Steps

18-(benzyloxy)octadecan-9-ol (6 g, 15.93 mmol), DMAP (0.195 g, 1.59 mmol) and TEA (2.9 ml, 20.71 mmol) in dry DCM (90 ml) were cooled to 0° C., then methanesulfonyl chloride (1.64 ml) was added under N2. The reaction was warmed to room temperature and stirring continued for another 3 h. The reaction mixture was diluted with DCM (100 ml), washed with 1N HCl, water, and brine solution and dried over MgSO4. The crude compound and imidazole (2.17 g, 31.86 mmol) were then heated at 70° C. for 16 h. The crude product was purified by silica gel column (1.5% MeOH in DCM) to give 1-(18-(benzyloxy)octadecan-9-yl)-1H-imidazole as a gummy liquid (2.22 g, 33%).

Provenance & Evidence