Furfural → 2-(6-Chloro-3-pyridyl)-1-(2-furyl)-1-ethanone

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To a mixture of 2-furaldehyde (7.9 g, 82.2 mmol) and zinc (II) iodide (110 mg, 0.345 mmol) was dropwise added trimethylsilyl cyanide (11.0 ml, 82.5 mmol) over 10 minutes at 0° C. under an atmosphere of nitrogen gas, followed by stirring as it was. After 30 minutes, the reaction mixture was diluted with tetrahydrofuran (200 ml) and then cooled to −78° C. A 1.0M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (86 ml, 86 mmol) was added dropwise thereto over 1 hour and then a solution of (6-chloro-3-pyridyl)methyl methanesulfonate (18.1 g, 81.7 mmol) in tetrahydrofuran (50 ml) was added dropwise over 1.5 hours thereto, followed by stirring while gradually elevated to room temperature. After 12.5 hours, a 1.0M solution of tetrabutylammonium fluoride in tetrahydrofuran (86 ml, 86 mmol) was added thereto, followed by stirring as it was. After further 30 minutes, the reaction mixture was diluted with a saturated aqueous ammonium chloride solution and ethyl acetate. The resulting organic layer was washed with a saturated aqueous ammonium chloride solution twice, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=10:1, 4:1, 3:1, and 2:1) and then suspended in hexane. Subsequently, the resulting precipitates were collected by filtration, to give the title compound (11.9 g, 54%) as a pale brown solid.

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