Dimethylformamide → (E)-7-(Phenylmethoxy)-8-(3-phenyl-2-propenyl)-4H-1-benzopyran-4-one

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Reaction Steps

A mixture of 8.76 g (30 mmol) of 7-(phenylmethoxy)-8-(2-propenyl)-4H-1-benzopyran-4-one (preceding example), 6.70 g (32.84 mmol) of iodobenzene, 5.11 g (30.84 mmol) of tetraethylammonium chloride, 8.94 g (91.22 mmol) of anhydrous sodium acetate, and 64 mL of dry N,N-dimethylformamide was stirred at room temperature while being purged with a stream of argon. Palladium(II) acetate (0.38 g; 1.7 mmol) was added and stirring was continued at room temperature, for 24 hr. The dark mixture was diluted with water and worked-up with ether in the usual manner (the ether extracts were additionally washed with 12% aqueous sodium bisulfite solution). Recrystallization of the crude product from acetonitrile afforded 6.13 g (55.5%) of the title compound as a brown solid. The analytical specimen was obtained from a separate experiment as yellow crystals, mp 131°-133° C.

Provenance & Evidence