Triethyl phosphonoacetate → ethyl (2E)-3-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}-2-propenoate

Participants

Reaction Steps

To a mixture of 3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde (0.80 g), ethyl diethylphosphonoacetate (0.40 g) and N,N-dimethylformamide (20 mL) was added sodium hydride (60% in oil, 0.080 g) under ice-cooling. The mixture was stirred at room temperature for 3 hrs. The reaction mixture was poured into ice water and the precipitated solid was collected by filtration to give ethyl (2E)-3-{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}-2-propenoate as pale-brown crystals (0.85 g, yield 96%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 177-178° C.

Provenance & Evidence