Ammonium Chloride → HCID 67987827, compound

Participants

Reaction Steps

1.0 M Tetrahydrofuran solution (28 ml) of lithium bis(trimethylsilyl)amide was added dropwise to a solution of tetrahydro-2H-pyrane-4-carboxylic acid methyl ester (2.87 g) in tetrahydrofuran (40 ml) at −78° C., and the mixture was stirred at the same temperature for an hour. And then a solution of 5-bromo-2-fluoropyridine (3.5 g) was added dropwise, and the reaction mixture was stirred at room temperature for two hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-(5-bromopyridin-2-yl)tetrahydro-2H-pyrane-4-carboxylic acid methyl ester (4.14 g) as a colorless oil.

Provenance & Evidence