Dimethylformamide → 1-[3-(benzyloxy)phenyl]-1H-1,2,4-triazole

Participants

Reaction Steps

To a sealable pressure tube, were added CuI (31 mg, 0.16 mmol), 1H-1,2,4-triazole (245 mg, 3.55 mmol), Potassium phosphate (1.37 g, 6.45 mmol), 1-(benzyloxy)-3-iodobenzene (1 g, 3.22 mmol), and a stir bar. The reaction vessel was fitted with a rubber septum, evacuated and back-filled with argon, and this sequence was repeated. DMF (3.22 mmol) and N,N′-dimethylethylene diamine (28 mg, 0.322 mmol) were then added successively under a stream of argon. The reaction tube was crimp sealed with a fresh PTFE septum (caution: build-up of pressure possible; use a safety shield) and immersed in a preheated oil bath at 110° C. for 24 h with magnetic stirring. The reaction mixture was removed from heating, allowed to attain ambient temperature, diluted with ethyl acetate (2-3 mL), filtered through a plug of silica gel, and eluted with additional ethyl acetate (10-20 mL). The filtrate was concentrated and the resulting residue was purified by chromatography on silica gel (80 gram biotage silica gel cartridge, 40-60% EtOAc hexanes) to provide the desired product as white solid. LRMS calc: 251.3; obs: 252.4 (M+1).

Provenance & Evidence