Triethylamine → 6-[4-(1-Phenylethenyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

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Reaction Steps

To a solution of 0.527 g (3.302 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.74 g (3.30 mmol) of 4-(1-phenylethenyl)benzoic acid and 1.84 ml (13.2 mmol) of triethylamine in 15 ml of N,N-dimethylformamide, 0.60 ml (3.96 mmol) of diethyl cyanophosphonate was added dropwise, followed by overnight stirring at room temperature. This mixture was poured into water and extracted with diethyl ether 3 times. The combined organic layer was dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1 to 3/1) to yield 6-[4-(1-phenylethenyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine.

Provenance & Evidence