Реакция #717767

Уравнение реакции

sodium cyclopentadienide

n-nonanophenone

→

6-(n-octyl)-6-phenylfulvene

Выход 72.5%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Другоеto produce a solution
2. 2
   Температураunder cooling with ice
3. 3
   ДругоеThen, the obtained deep red solution was quenched with dilute aqueous hydrochloric acid
4. 4
   Температураunder cooling with ice
5. 5
   workup.ADDITIONThen, 30 mL of diethyl ether was added
6. 6
   Экстракцияthe soluble part in diethyl ether was extracted
7. 7
   Промывкаwashed with an aqueous solution of saturated sodium hydrogen carbonate, water
8. 8
   workup.DISTILLATIONThe solvent was distilled off
9. 9
   Другоеthe residue was purified by silica gel column chromatography
10. 10
    Другоеto obtain an objective that

Методика

Under a nitrogen atmosphere, 2.0 g (9.2 mmol) of n-nonanophenone and 30 mL of dry THF were put into a 100-mL Schlenk flask to produce a solution. To this solution, 5.6 mL (11.2 mmol) of a solution of 2.0-M sodium cyclopentadienide in THF was added under cooling with ice, and the product was stirred at room temperature for 19 hours. Then, the obtained deep red solution was quenched with dilute aqueous hydrochloric acid under cooling with ice. Then, 30 mL of diethyl ether was added thereto, and the soluble part in diethyl ether was extracted, and the organic layer was neutralized and washed with an aqueous solution of saturated sodium hydrogen carbonate, water, and a saturated salt solution and then dehydrated with anhydrous magnesium sulfate. The solvent was distilled off, and then the residue was purified by silica gel column chromatography to obtain an objective that was a red liquid (amount: 1.77 g and yield: 72.5%).

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