Triethyl phosphonoacetate → HCID 46941678, compound

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.

1. stirringthe mixture was stirred under a nitrogen atmosphere at room temperature for 1 hr
2. customThe reaction was quenched with saturated ammonium chloride solution (50 ml)
3. customthe reaction solution was partitioned between ethyl acetate (900 mL) and water (900 mL)
4. washThe organic layer was washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 90:10-85:15)

ORD record

ord-85955d99a56a42e6a29bac2449ed4784

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08338622B2