반응 #717767

반응 방정식

sodium cyclopentadienide

n-nonanophenone

→

6-(n-octyl)-6-phenylfulvene

수율 72.5%

용매

THF

THF

반응 조건

후처리

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

실험 절차

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%).

출처