Ammonium Chloride → HCID 58201208, compound

Participants

Reaction Conditions

Reaction Steps

The above 5-bromo-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-methoxy-3-methylpyridine (734 mg) was dissolved in tetrahydrofuran (30 ml), and butyllithium (1.59 M solution, 2.42 ml) was then added dropwise to the solution at −110° C. The resulting mixture was stirred at the same above temperature for 1 hour, and a tetrahydrofuran (5 ml) solution of N-fluorobenzenesulfonimide (3.03 g) was then added dropwise to the reaction solution at the same temperature. The temperature of the resulting mixture was gradually raised to −68° C. over 3 hours, and the mixture was then stirred at room temperature for 30 minutes. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and the filtrate was then concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain the title compound (353 mg) as an oily substance.

Provenance & Evidence