Sodium hydride → 2,3-Dihydrofuro[3,2-b]pyridine

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Reaction Steps

To a suspension of 60% sodium hydride (11.4 g, 286 mmol) in DMSO (170 mL) was added trimethylsulfonium iodide (29.9 g, 136 mmol), and the mixture was stirred at room temperature for 30 min. A solution of (3-hydroxypyridin-2-yl)-N,N,N-trimethylmethanaminium iodide (40.0 g, 136 mmol) in DMSO (130 mL) was added dropwise thereto, and the mixture was further stirred at room temperature for 2 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. 1M Hydrochloric acid was added to the extract, and the mixture was extracted with water. The extract was basified with 1M aqueous sodium hydroxide solution and extracted again with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80→50/50) to give the title compound (7.77 g, yield 47%).

Provenance & Evidence