反応 #43633

反応方程式

water

7-bromo-3,4-dihydro-1(2H)-isoquinolinone

2,4,6-trivinylcyclotriboroxane

water

K2CO3

→

product

収率 88.0%

7-ethenyl-3,4-dihydro-1(2H)-isoquinolinone

収率 88.0%

溶媒

1,2-dimethoxyethane

反応条件

後処理

1. 1
   温度The reaction was heated
2. 2
   温度at reflux for 1.5 h
3. 3
   抽出The mixture was extracted with 10% methanol/dichloromethane (3×100 ml)
4. 4
   乾燥the organic layers were dried with magnesium sulphate
5. 5
   その他evaporated
6. 6
   洗浄Chromatography on silica, eluting with 0-100% ethyl acetate/hexane

実験手順

A solution of 7-bromo-3,4-dihydro-1(2H)-isoquinolinone (0.679 g, 3.004 mmol) and tetrakis(triphenylphosphine)palladium(0) (174 mg, 0.150 mmol) in 1,2-dimethoxyethane (30 ml) was stirred at room temperature for 0.5 h before addition of 2,4,6-trivinylcyclotriboroxane.pyridine complex (for a synthesis see Kerins, Fergal; O'Shea, Donal F. J. Org. Chem. (2002), 67(14), 4968) (295 mg, 1.218 mmol), K2CO3 (415 mg, 3.004 mmol) and water (10 ml). The reaction was heated at reflux for 1.5 h before cooling to room temperature and addition of water (50 ml). The mixture was extracted with 10% methanol/dichloromethane (3×100 ml), the organic layers were dried with magnesium sulphate and evaporated. Chromatography on silica, eluting with 0-100% ethyl acetate/hexane, gave the product (456 mg, 88%).

出典