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

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Reaction Steps

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%)).

Provenance & Evidence