Dimethylformamide → 5-(4-Methoxyphenyl)-4-methylnicotinaldehyde

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Reaction Steps

A n-butyllithium-1.58M n-hexane solution (3.9 ml, 6.13 mmol) was added dropwise to a solution of 3-bromo-5-(4-methoxyphenyl)-4-methylpyridine (1.55 g, 5.57 mmol) obtained in Example (76-1) in tetrahydrofuran (20 ml) at −78° C., and the mixture was stirred for 5 minutes. N,N-Dimethylformamide (0.87 ml, 11.2 mmol) was added dropwise thereto at the same temperature and the mixture was stirred for 30 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture and the temperature of the mixture was raised to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1-2/3) to give 5-(4-methoxyphenyl)-4-methylnicotinaldehyde (0.56 g, yield: 44%).

Provenance & Evidence