Dimethylformamide → HCID 86605922, compound

Participants

Reaction Steps

A mixture of ethyl (4-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)acetate (3.00 g), [(1-ethyl-1H-imidazol-4-yl)methyl](triphenyl)phosphonium chloride hydrochloride (3.43 g), anhydrous potassium carbonate (1.07 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 16 hrs. To the reaction mixture were added [(1-ethyl-1H-imidazol-4-yl)methyl](triphenyl)phosphonium chloride hydrochloride (1.14 g) and anhydrous potassium carbonate (356 mg) and the mixture was stirred at room temperature for 2 days. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (9:1 to 1:0, v/v) to give ethyl (4-{4-[(4-[({4-[(E)-2-(1-ethyl-1H-imidazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}phenyl)acetate as colorless crystals. Recrystallization from ethyl acetate-hexane gave colorless crystals (352 mg, yield 10%). melting point: 140-141° C.

Provenance & Evidence