1,3-Diphenyl-2-propanone → 6,6-Dibenzylfulvene

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%)).

1. temperatureThis mixture solution was cooled in an ice bath
2. stirringThereafter, the mixture was stirred at room temperature for 3 hours
3. temperatureThe thus obtained white slurry was cooled in an ice bath
4. customa solution prepared
5. additionwas added
6. stirringSubsequently, the mixture was stirred at room temperature for 12 hours
7. customThe resulting yellow solution was quenched with a saturated aqueous solution of NH4Cl
8. extractionThe soluble fraction was extracted with 100 mL of hexane
9. washthis organic phase was washed with water and saturated brine
10. dry with materialdried over magnesium sulfate
11. distillationThe solvent was distilled off
12. customthe residue was purified by column chromatography

ORD record

ord-c9dfb31229ba49e584cb559fff7f11e2

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382356B2