Reaction #717767

Reaction equation

sodium cyclopentadienide

n-nonanophenone

→

6-(n-octyl)-6-phenylfulvene

Yield 72.5%

Solvents

THF

THF

Conditions

Workup

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

Procedure

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%).

Source