Triethylamine → 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one

Participants

Reaction Steps

To a solution of 0.270 g (1.692 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.36 g (1.9 mmol) of 6-phenylhexanoic acid and 0.94 ml (6.8 mmol) of triethylamine in 30 ml of dichloromethane, 0.39 ml (2.5 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (hexane/ethyl acetate=6/1 to 3/1) to yield the desired product.

Provenance & Evidence