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

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Reaction Steps

To a solution of 0.552 g (3.458 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.78 g (3.46 mmol) of 4-phenethylbenzoic acid and 1.93 ml (13.8 mmol) of triethylamine in 15 ml of N,N-dimethylformamide, 0.63 ml (4.15 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-phenethylbenzoyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine.

Provenance & Evidence