反応 #8288

反応方程式

3-Methoxy-phenyl-boronic acid

tetrahydrofuran

sodium carbonate

→

title compound

4-(3-Methoxy-phenyl)-5H-furan-2-one

溶媒

ether

water

反応条件

後処理

1. 1
   その他de-gassed for 15 min
2. 2
   温度The reaction mixture is refluxed for 45 min
3. 3
   ろ過filtered through a Celite® pad
4. 4
   洗浄The filtrate is washed with water and brine
5. 5
   乾燥dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The residue is chromatographed on SiO2 (3:7 ethyl acetate/hexanes)

実験手順

3-Methoxy-phenyl-boronic acid (2.16 g, 14.2 mmol) and trifluoromethansulfonic acid 5-oxo-2,5-dihydro-furan-3-yl ester1 (3 g, 12.92 mmol) in tetrahydrofuran (110 mL) is dissolved and de-gassed for 15 min. To this solution is added sodium carbonate (3.42 g, 32.3 mmol) in water (10 mL) and tetrakis-triphenylphosphine-palladium(0) (0.75 g, 0.646 mmol). The reaction mixture is refluxed for 45 min, cooled to room temperature, diluted with ether (50 mL) and filtered through a Celite® pad. The filtrate is washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue is chromatographed on SiO2 (3:7 ethyl acetate/hexanes) to yield the title compound, 1.9 g (71%), as a white crystalline solid.

出典