Imidazole → 4-(2-((tert-Butyldimethylsilyl)oxy)ethyl)-1-trityl-1H-imidazole

Participants

Reaction Steps

To a solution of 2-(1-trityl-1H-imidazol-4-yl)-ethanol (5.21 g, 14.7 mmol) in DMF (20 mL) is added tert-butylchlorodimethylsilane (2.44 g, 16.1 mmol), dimethylaminopyridine (0.179 g, 1.47 mmol) and imidazole (3.00 g, 44.1 mmol). The reaction mixture is stirred for 2 h at room temperature. It is then diluted with ethyl acetate and washed with water thrice. The organic phase is dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (hexane-ethanol, 7:3) to give 4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-trityl-1H-imidazole product, which is used in the next step without further purification; MS (ESI) m/z 469.3 (M+H)

Provenance & Evidence