Triethyl phosphonoacetate → HCID 46941678, compound

Participants

Reaction Steps

To a solution (200 ml) of ethyl diethylphosphonoacetate (10.5 g) in N,N-dimethylformamide was added sodium hydride (60% in oil, 1.87 g), and the mixture was stirred under a nitrogen atmosphere at room temperature for 15 min. To this solution was added a solution of 5-bromo-2-furaldehyde (7.45 g) in N,N-dimethylformamide (40 ml), and the mixture was stirred under a nitrogen atmosphere at room temperature for 1 hr. The reaction was quenched with saturated ammonium chloride solution (50 ml) and the reaction solution was partitioned between ethyl acetate (900 mL) and water (900 mL). The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-85:15) to give the title compound (10.0 g, yield 96%) as a pale-yellow solid.

Provenance & Evidence