反応 #68746

反応方程式

2-bromo-3-methoxycyclopent-2-enone

4′-chloro-4-ethylbiphen-3-ylboronic acid

potassium phosphate

→

2-(4′-chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone

収率 75.5%

反応条件

後処理

1. 1
   その他degassed toluene (25 ml) under an atmosphere of nitrogen
2. 2
   温度to cool to room temperature
3. 3
   その他quenched with water (40 ml)
4. 4
   抽出extracted with ethyl acetate (3×30 ml)
5. 5
   洗浄washed with brine (15 ml)
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   ろ過filtered
8. 8
   その他the filtrate is evaporated under reduced pressure
9. 9
   その他The residue is purified by column chromatography on silica gel

実験手順

To a stirred suspension of 2-bromo-3-methoxycyclopent-2-enone (1.0 g, 5.23 mmol), 4′-chloro-4-ethylbiphen-3-ylboronic acid (2.03 g, 7.80 mmol) and potassium phosphate (2.23 g, 10.50 mmol) in anhydrous, degassed toluene (25 ml) under an atmosphere of nitrogen is added palladium(II)acetate (24 mg, 0.105 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (86 mg, 0.209 mmol). The reaction is heated at 90° C. for 4 hours and then allowed to cool to room temperature, quenched with water (40 ml) and extracted with ethyl acetate (3×30 ml). The organic extracts are combined, washed with brine (15 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2-(4′-chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone (1.29 g, 75%).

出典