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

In an atmosphere of nitrogen, 8.0 g (121.0 mmol) of cyclopentadiene and 100 ml of dehydrated THF were placed in a 500 ml three-necked flask, and they were stirred. This mixed solution was cooled in an ice bath, and to the mixed solution was added 80 ml (125.6 mmol) of a hexane solution of n-butyllithium having a concentration of 15.7 mol/liter. Thereafter, the mixture was stirred at room temperature for 3 hours, and the resulting white slurry was cooled in an ice bath, followed by adding a solution obtained by dissolving 25.0 g (118.0 mmol) of 1,3-diphenyl-2-propanone in 50 ml of dehydrated THF. Thereafter, the mixture was stirred at room temperature for 12 hours, and the resulting yellow solution was quenched with a saturated NH4Cl aqueous solution. Then, 100 ml of hexane was added to extract a soluble matter, and this organic phase was washed with water and a saturated saline solution, followed by drying using magnesium sulfate. Then, the solvent was distilled off, and the residue was purified by column chromatography to obtain a desired product of a yellow solid.

1. temperatureThis mixed solution was cooled in an ice bath
2. stirringThereafter, the mixture was stirred at room temperature for 3 hours
3. temperaturethe resulting white slurry was cooled in an ice bath
4. additionby adding a solution
5. customobtained
6. stirringThereafter, the mixture was stirred at room temperature for 12 hours
7. customthe resulting yellow solution was quenched with a saturated NH4Cl aqueous solution
8. additionThen, 100 ml of hexane was added
9. extractionto extract a soluble matter
10. washthis organic phase was washed with water
11. customby drying
12. distillationThen, the solvent was distilled off
13. customthe residue was purified by column chromatography

ORD record

ord-1e2adc799bee4ad4ad9641da99ef79ca

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08293856B2