Imidazole → tert-Butyl((5-iodopentyl)oxy)dimethylsilane

Participants

Reaction Steps

To a mixture of imidazole (1.13 g, 16.6 mmol), triphenyl phosphine (2.16 g, 8.24 mmol), and iodine (1.92 g, 7.56 mmol) in a mixed solvent of toluene (40 mL) and acetonitrile (4 mL) was added 5-t-butyldimethylsilyloxy-1-pentanol (1.5 g, 6.87 mmol). The mixture was stirred for 1 h at room temperature and aqueous Na2SO3 was added. The mixture was extracted with ethyl acetate and the extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 10:1 hexane/ethyl acetate to give the title compound (1.55 g, 69%).

Provenance & Evidence