반응 #1137859

반응 방정식

hexane

n-butyllithium

cyclopentadiene

1,3-diphenyl-2-propanone

→

product

수율 12.1%

6,6-dibenzylfulvene

수율 12.1%

용매

THF

THF

반응 조건

후처리

1. 1
   온도This mixture solution was cooled in an ice bath
2. 2
   workup.STIRRINGThereafter, the mixture was stirred at room temperature for 3 hours
3. 3
   온도The thus obtained white slurry was cooled in an ice bath
4. 4
   기타a solution prepared
5. 5
   workup.ADDITIONwas added
6. 6
   workup.STIRRINGSubsequently, the mixture was stirred at room temperature for 12 hours
7. 7
   기타The resulting yellow solution was quenched with a saturated aqueous solution of NH4Cl
8. 8
   추출The soluble fraction was extracted with 100 mL of hexane
9. 9
   세척this organic phase was washed with water and saturated brine
10. 10
    건조dried over magnesium sulfate
11. 11
    workup.DISTILLATIONThe solvent was distilled off
12. 12
    기타the residue was purified by column chromatography

실험 절차

Under a nitrogen atmosphere, a 500-mL three-necked flask was charged with 8.0 g (121.0 mmol) of cyclopentadiene and 100 mL of dehydrated THF, and the mixture was stirred. This mixture solution was cooled in an ice bath, and 80 mL (125.6 mmol) of a 1.57 mol/L hexane solution of n-butyllithium was added. Thereafter, the mixture was stirred at room temperature for 3 hours. The thus obtained white slurry was cooled in an ice bath, and then a solution prepared by dissolving 25.0 g (118.0 mmol) of 1,3-diphenyl-2-propanone in 50 mL of dehydrated THF was added. Subsequently, the mixture was stirred at room temperature for 12 hours. The resulting yellow solution was quenched with a saturated aqueous solution of NH4Cl. The soluble fraction was extracted with 100 mL of hexane, and this organic phase was washed with water and saturated brine, and then dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography to give a target product as a yellow solid (yield 3.7 g (12%)).

출처