2-{[4-(Trimethylsilyl)but-3-yn-1-yl]oxy}pyrimidine → 4-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine

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Reaction Steps

A solution of 2-{[4-(trimethylsilyl)but-3-yn-1-yl]oxy}pyrimidine (116 g, 524 mmol) in nitrobenzene (1000 mL) was stirred at 200° C. for 24 hr. The solvent was removed by silica gel column chromatography (ethyl acetate/hexane=13/87→50/50). The residue was diluted with ethyl acetate, and the mixture was extracted twice with 1M hydrochloric acid. The aqueous layer was neutralized with 8M aqueous sodium hydroxide solution and extracted with ethyl acetate. The solvent was evaporated under reduced pressure to give the title compound (16.2 g, yield 14%).

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