Benzyl azide → 2-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde

Participants

Reaction Steps

A solution of 2-ethynylbenzaldehyde (200 mg, 1.54 mmol) and benzyl azide (0.38 mL, 3.0 mmol) in 2.0 mL of N,N-dimethylformamide was stirred at 80° C. overnight. The reaction mixture was diluted with water, and the solution was extracted with a 5:1 solution (12 mL) of ethyl acetate and hexane. The extract was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain 2-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde (259 mg, 65%) and 2-(1-benzyl-1H-1,2,3-triazol-5-yl)benzaldehyde (118 mg, 30%).

Provenance & Evidence