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

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Reaction Steps

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.

Provenance & Evidence