Dimethylformamide → HCID 86605914, compound

Participants

Reaction Steps

To a mixture of 3-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}benzonitrile (2.50 g), tetraethyl methylenediphosphonate (1.53 g) and N,N-dimethylformamide (50 mL) was added sodium hydride (60% in oil, 0.23 g) at room temperature. The mixture was stirred at room temperature for 2 hrs. Water was poured into the reaction mixture, 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 to give diethyl [(E)-2-{3-[(4-{[2-(3-cyanophenyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}ethenyl]phosphonate as colorless crystals (2.20 g, yield 70%) from a fraction eluted with ethyl acetate-hexane (4:1 to 9:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 147-148° C.

Provenance & Evidence