1H-1,2,4-Triazole → 3,5-Diethoxy-4-[1,2,4]triazol-1-yl-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-diethoxy-4-fluoro-benzaldehyde (5.00 g, 23.56 mmol, 1.0 equiv; intermediate 21) in DMSO (50 mL) was added 1H-[1,2,4]triazole (3.26 g, 47.12 mmol, 2.0 equiv) and K2CO3 (6.51 g, 47.12 mmol, 2.0 equiv) and the reaction mixture stirred at 110° C. for 1 h. The solution was poured on crashed ice, the reaction mixture extracted with ethyl acetate (2×50 mL) and the combined organic phases dried over MgSO4. The organic solvent was evaporated under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with a gradient of heptane/ethyl acetate (1:1→0:1) providing 5.28 g (86%) of the title compound. MS (ESI): 261.9 [M+H]+.

Provenance & Evidence