反应详情

A mixture of ethyl 3-bromobenzoate (1.0 g, 4.37 mmol), ethynyl trimethylsilane (644 mg, 6.56 mmol), diisopropylamine (929 mg, 9.20 mmol), cuprous iodide(I) (16.6 mg, 0.0872 mmol), and bis(triphenylphosphine) palladium(II) chloride (123 mg, 0.175 mmol) was heated at 45° C. for 5 h in dried THF (8 ml) under argon atmosphere. After cooling, the reaction was quenched by the addition of water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=50/1) to give ethyl 3-[(trimethylsilyl)-ethynyl]benzoate (90%)

1. temperatureAfter cooling
2. customthe reaction was quenched by the addition of water
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. customThe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=50/1)