Dibenzoylmethane → 2-[(Dimethylamino)methylidene]-1,3-diphenylpropane-1,3-dione

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Reaction Steps

To a solution of dibenzoylmethane (1.072 g, 4.78 mmol) in 6 mL of toluene was added neat N,N-dimethylformamide dimethylacetal (0.7 mL, 630 mg, 5.25 mmol) dropwise via syringe. The resulting solution was stirred at rt for 1 h and then heated at reflux for 16 h. Once at rt, the reaction was concentrated in vacuo. The residue was dissolved in a minimum of CH2Cl2 and added to 13 cm of flash silica gel in a 5 cm dia. column. Elution with 1 L of 1%, 500 mL of 2% and 300 mL of 3% MeOH/CH2Cl2 gave 975 mg of the desired product as a semisolid. Trituration with 50 mL of hexanes gave 772 mg of the title compound as a light yellow solid, mp 123-124° C. (lit mp 120° C., Schenone, P. et al. J. Het. Chem. 1982,19(6), 1355-61).

Provenance & Evidence