Potassium Sodium Tartrate → {5-Chloro-6-[(1,3-difluoropropan-2-yl)oxy]pyridin-3-yl}methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-chloro-6-[(1,3-difluoropropan-2-yl)oxy]nicotinate (1 g) in THF (20 mL) was added dropwise a 0.99 M solution of DIBAL in toluene (11.3 mL) at 0° C., followed by stirring at 0° C. for 2 hours. Then, the reaction solution was poured into an aqueous Rochelle salt solution, followed by stirring at room temperature for 1 hour. After extraction with an EtOAc-water system, the organic layer was washed with brine, dried over MgSO4, and then filtered, and the desiccant was removed. The vehicle was evaporated under reduced pressure, followed by purification by silica gel column chromatography (Hex:AcOEt=98:2 to 70:30) to obtain {5-chloro-6-[(1,3-difluoropropan-2-yl)oxy]pyridin-3-yl}methanol (650 mg) as a colorless liquid.

Provenance & Evidence