反応 #1552094

反応方程式

3-iodoaniline

3,3-dimethyl-1-butyne

water

→

crude product

3-(3,3-dimethylbut-1-yn-1-yl)aniline

溶媒

triethylamine

反応条件

後処理

1. 1
   温度With ice-cooling
2. 2
   その他remains at 20° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   濃縮The reaction solution is concentrated under reduced pressure
5. 5
   その他the residue formed
6. 6
   抽出The mixture is then extracted three times with diethyl ether
7. 7
   洗浄The combined organic phases are once more washed with water
8. 8
   乾燥dried with sodium sulphate
9. 9
   濃縮concentrated under reduced pressure

実験手順

1.05 g (1.5 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.26 g (1.5 mmol) of copper(I) iodide are added to a solution consisting of 5.47 g (25 mmol) of 3-iodoaniline in 40 ml of triethylamine. With ice-cooling, 3.08 g (37.5 mmol) of 3,3-dimethyl-1-butyne are added dropwise such that the temperature remains at 20° C. After the addition has ended, the mixture is stirred at 20° C. for 20 hours. The reaction solution is concentrated under reduced pressure and the residue formed is stirred into 1 l of water. The mixture is then extracted three times with diethyl ether. The combined organic phases are once more washed with water, dried with sodium sulphate and concentrated under reduced pressure. The crude product obtained is purified by silica gel chromatography (mobile phase methylene chloride). This gives 2.70 g (60% of theory) of 3-(3,3-dimethylbut-1-yn-1-yl)aniline having a content of 97% according to HPLC. log P=2.71.

出典