反応 #577216

反応方程式

sodium carbonate

phenylboronic acid

1-chloroisoquinoline

toluene

→

1-phenylisoquinoline

収率 43.0%

溶媒

ethanol

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度Thereafter, reflux
3. 3
   その他After completion of the reaction
4. 4
   温度the reaction product was cooled
5. 5
   抽出extracted by addition of cold water and toluene
6. 6
   洗浄The organic layer was washed with saline water
7. 7
   その他dried on magnesium sulfate
8. 8
   その他followed by removal of the solvent under a reduced pressure
9. 9
   その他to provide
10. 10
    その他dry solid
11. 11
    その他The residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1)

実験手順

In a 100 ml-three-necked flask, 3.04 g (24.9 mmole) of phenylboronic acid (made by Tokyo Kasei), 4.0 g of (25.0 mmole) of 1-chloroisoquinoline, 25 ml of toluene, 12.5 ml of ethanol and 25 ml of 2M-sodium carbonate aqueous solution were placed and stirred at room temperature under nitrogen stream, and 0.98 g (0.85 mmole) of tetrakis(triphenylphosphine)palladium (0) was added thereto. Thereafter, reflux under stirring was performed for 8 hours under nitrogen stream. After completion of the reaction, the reaction product was cooled and extracted by addition of cold water and toluene. The organic layer was washed with saline water and dried on magnesium sulfate, followed by removal of the solvent under a reduced pressure to provide dry solid. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1) to obtain 2.20 g (yield=43.0%) of 1-phenylisoquinoline. FIG. 7 shows a 1H-NMR spectrum of a solution of the compound in heavy chloroform.

出典