反应详情

温度

130 °C

A mixture of 201 mg (0.57 mmol) of the above 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one, 144 mg (1.22 mmol) of zinc cyanide and 24 mg (0.021 mmol) of tetrakis(triphenylphosphine)palladium(0) in 2 mL of DMF was warmed at 130° C. After 36 hours, the mixture was cooled, diluted with 10 mL of saturated aqueous ammonium chloride, and extracted with three 7 mL portions EtOAc. The combined organic layers were washed with three 7 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was adsorbed onto silica gel and chromatographed on silica gel using EtOAc-hexanes (0:100, then 1:99, then 2:98, then 3:97, then 4:96) to afford 102 mg (60%) of 7-(4,4,4-trifluoro-1,1-dimethyl-3-oxobutyl)-2,3-dihydrobenzofuran-5-carbonitrile as a white solid.

1. temperaturethe mixture was cooled
2. extractionextracted with three 7 mL portions EtOAc
3. washThe combined organic layers were washed with three 7 mL portions of brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customchromatographed on silica gel