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

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Reaction Steps

To a solution of 0.39 g (2.2 mmol) of 6-phenylhexan-1-ol and 0.38 ml (2.7 mmol) of triethylamine in 20 ml of ether, methanesulfonyl chloride was added dropwise under ice-cooling, followed by stirring for 10 minutes. The ether solution was washed with water and saturated aqueous sodium chloride, after which it was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The residual oil (crude 6-phenylhexyl methanesulfonate) was dissolved in 30 ml of acetonitrile; 0.289 g (1.811 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride and 0.76 ml (5.4 mmol) of triethylamine were added, followed by refluxing for 3 hours. The solvent was distilled off from the reaction mixture under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1) to yield the desired product.

Provenance & Evidence