Formaldehyde → HCID 68430386, compound

Participants

Reaction Steps

To a solution of 4-methylpyridin-2-ol (1.0 g) in chloroform (10 ml), 1.37 ml of 2-iodopropane and 3.8 g of silver carbonate (II) were added, and the reaction solution was stirred at room temperature for 24 hours. The reaction solution was Celite-filtered, and the filtrate was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in tetrahydrofuran (8 ml), 7.2 ml of N-butyllithium (1.5M hexane solution) was added at −78° C., and the reaction solution was stirred at the same temperature for 30 minutes and then stirred at room temperature for 15 minutes. The reaction solution was recooled to −78° C., 324 mg of paraformaldehyde was added, and the reaction solution was stirred for 3 hours while increasing the temperature of the reaction solution to room temperature. To the reaction solution was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50)) to afford the title compound as a yellow oil.

Provenance & Evidence