2-Iodoxybenzoic acid → 3-[4-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]propanal

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Reaction Steps

A mixture of 3-[4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]propan-1-ol (6.54 g, 26.0 mmol) and orthoiodoxybenzoic acid (9.47 g, 33.8 mmol) in dimethyl sulfoxide (80 mL) was stirred at room temperature for 5 hr. The reaction solution was diluted with diethyl ether, and the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and 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=30/70→70/30) to give the title compound (5.69 g, yield 87%).

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