反应 #89963

反应方程式

trimethylsilylacetylene

2-bromomethyl-4-methoxy-benzoic acid methyl ester

triphenylphosphine

cesium carbonate

ammonium chloride

→

title compound

收率 54.0%

4-Methoxy-2-(3-trimethylsilanylprop-2-ynyl)-benzoic acid methyl ester

收率 54.0%

溶剂

THF

反应条件

后处理

1. 1
   其他degassed
2. 2
   其他flushed with nitrogen gas
3. 3
   萃取followed by extraction with ethyl acetate
4. 4
   洗涤The organic layer was washed with brine
5. 5
   干燥dried over magnesium sulfate
6. 6
   其他The drying agent was removed by filtration
7. 7
   其他the residues obtained
8. 8
   浓缩after concentration under reduced pressure
9. 9
   其他were purified by silica gel column chromatography (ethyl acetate/hexane)

实验过程

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%).

来源