反应详情

温度

110 °C

Under a nitrogen atmosphere, sodium carbonate (78 mg, 0.7 mmol), palladium tetrakis(triphenylphosphine) (81 mg, 0.07 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (182 mg, 0.7 mmol) were added to a solution of ethyl (4-bromo-2,5-dimethyl-thiophen-3-yl)-oxo-acetate (17c) (200 mg, 0.69 mmol) in a mixture of water (3.5 mL) and N,N-dimethylformamide (11 mL). The mixture was heated at 110° C. for 1 hour. The mixture was then cooled at room temperature, concentrated in vacuo and water (30 mL) was added. The aqueous layer was extracted with ethyl acetate (2×30 mL). The organic layer was washed with brine (30 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired product (17d) as a white solid (90 mg, 0.26 mmol, 38%).

1. temperatureThe mixture was then cooled at room temperature
2. concentrationconcentrated in vacuo and water (30 mL)
3. additionwas added
4. extractionThe aqueous layer was extracted with ethyl acetate (2×30 mL)
5. washThe organic layer was washed with brine (30 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated under reduced pressure
9. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)