Formamide → 2-(5-Fluorobenzofur-7-yl)propionamide

Temperature

100 °C

To a solution of 0.27 gm (1.15 mMol) ethyl 2-(5-fluorobenzofur-7-yl)propionate in 4 mL dimethylformamide were added sequentially 0.16 mL (3.91 mMol) freshly distilled formamide and 0.81 mL (0.80 mMol) sodium methoxide (1 M in methanol) dropwise and the resulting mixture was heated at 100° C. for 45 minutes. The reaction mixture was cooled to room temperature and was then diluted with 25 volumes of ethyl acetate. The mixture was then washed sequentially with water and saturated aqueous sodium chloride, and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with 2:1 ethyl acetate:hexane. Fractions containing product were combined and concentrated under reduced pressure to provide 0.060 gm (25%) of the desired compound.

1. temperatureThe reaction mixture was cooled to room temperature
2. washThe mixture was then washed sequentially with water and saturated aqueous sodium chloride
3. concentrationconcentrated under reduced pressure
4. washeluting with 2:1 ethyl acetate
5. additionFractions containing product
6. concentrationconcentrated under reduced pressure

ORD record

ord-813138b3309c42589e021090076a0b54

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07045545B1