Ethyl Acetate → N-[3-fluoro-5-(pyridin-3-yloxy)phenyl]-2-(hydroxymethyl)benzenesulfonamide

Participants

Reaction Steps

A solution of 1.0M diisobutylaluminum hydride in tetrahydrofuran (7.50 ml) was added to a solution of methyl 2-({[3-fluoro-5-(pyridin-3-yloxy)phenyl]amino}sulfonyl)benzoate (1.50 g) in tetrahydrofuran (22 ml) at 0° C., and the reaction solution was stirred at the same temperature for 1 hour. A saturated aqueous solution of Rochelle salt and ethyl acetate were added to the reaction solution, and the mixture was stirred for 30 minutes, followed by being extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel chromatography to yield the title compound as a colorless oily substance.

Provenance & Evidence