Реакция #1945076

Уравнение реакции

(trimethylsilyl)acetylene

diethylamine

4-(trans-4-propylcyclohexyl)-1-(2-iodoethynyl)benzene

→

4-(trans-4-propylcyclohexyl)-1-(4-trimethylsilyl-1,3-butadiyne-1-yl)benzene

Выход 24.0%

Растворители

water

Условия реакции

Обработка

1. 1
   workup.STIRRINGfurther stirred at room temperature for 15 minutes
2. 2
   workup.STIRRINGstirred at room temperature overnight
3. 3
   workup.ADDITIONwas added
4. 4
   Экстракцияextracted with toluene twice
5. 5
   ДругоеThe organic layer thus obtained
6. 6
   Промывкаwas washed with water
7. 7
   Сушкаdried over anhydrous magnesium sulfate
8. 8
   ФильтрацияAfter it was subjected to filtration
9. 9
   workup.DISTILLATIONthe solvent was distilled off under a reduced pressure
10. 10
    ДругоеThe residue was purified by column chromatography (silica gel/heptane) and recrystallization (ethanol)

Методика

To a mixture of dichlorobistriphenylphosphine palladium (4.2 mmol) and copper iodide (0.64 mmol) was added diethylamine, and stirred at room temperature under argon gas atmosphere for 30 minutes. Then, 4-(trans-4-propylcyclohexyl)-1-(2-iodoethynyl)benzene (0.12 mol) was added thereto, and further stirred at room temperature for 15 minutes. To this reaction mixture was added (trimethylsilyl)acetylene (0.14 mol), and stirred at room temperature overnight. After completion of the reaction, water was added thereto and extracted with toluene twice. The organic layer thus obtained was washed with water, and then dried over anhydrous magnesium sulfate. After it was subjected to filtration, the solvent was distilled off under a reduced pressure. The residue was purified by column chromatography (silica gel/heptane) and recrystallization (ethanol) to obtain colorless crystals of 4-(trans-4-propylcyclohexyl)-1-(4-trimethylsilyl-1,3-butadiyne-1-yl)benzene. (Yield 24%).

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