反应详情

温度

55 °C

To the THF (16 ml) solution of 2-bromomethyl-4-methoxy-benzoic acid methyl ester (961 mg, 4.09 mmol), triphenylphosphine (107 mg, 0.1 eq.), cesium carbonate (1.87 g, 1.4 eq.), copper iodide (59 mg, 0.076 eq.) and tris(dibenzylideneacetone)dipalladium (86 mg, 0.023 eq.) were added, degassed, flushed with nitrogen gas, added with trimethylsilylacetylene (734 μl, 1.3 eq.), and then stirred overnight at 55° C. To the reaction solution, saturated aqueous solution of ammonium chloride was added followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (brown oily substance, 606 mg, 54%).

1. customdegassed
2. customflushed with nitrogen gas
3. extractionfollowed by extraction with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried over magnesium sulfate
6. customThe drying agent was removed by filtration
7. customthe residues obtained
8. concentrationafter concentration under reduced pressure
9. customwere purified by silica gel column chromatography (ethyl acetate/hexane)