Реакция #1552094

Уравнение реакции

3-iodoaniline

3,3-dimethyl-1-butyne

water

→

crude product

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

Растворители

triethylamine

Условия реакции

Обработка

1. 1
   ТемператураWith ice-cooling
2. 2
   Другоеremains at 20° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   КонцентрированиеThe reaction solution is concentrated under reduced pressure
5. 5
   Другоеthe residue formed
6. 6
   ЭкстракцияThe mixture is then extracted three times with diethyl ether
7. 7
   ПромывкаThe combined organic phases are once more washed with water
8. 8
   Сушкаdried with sodium sulphate
9. 9
   Концентрированиеconcentrated under reduced pressure

Методика

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.

Источник