Ammonium Chloride → HCID 86692510, compound

Participants

Reaction Steps

To a solution of tetrahydro-2H-pyran-4-carboxylic acid methyl ester (759 mg) in toluene (5 ml) was added dropwise a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (5.26 ml) under ice-cooling, and stirred at the same temperature for 1 hour. Then, a solution of 5-bromo-2-fluoro-3-methylpyridine (1 g) in toluene (5 ml) was added dropwise thereto, and stirred at room temperature for 2 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added thereto, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid methyl ester (753 mg) as a pale yellow oil. MS (ESI) m/z: 314, 316 (M+H)+.

Provenance & Evidence