Reacción #43324

Ecuación de reacción

toluene

diisobutylaluminium hydride

2-ethoxycarbonyl-5-difluoromethoxypyridine

sodium borohydride

Sodium sulfate decahydrate

→

title compound

Rendimiento 87.0%

5-difluoromethoxy-2-hydroxymethylpyridine

Rendimiento 87.0%

Disolventes

THF

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred at 0° C. for 30 minutes
2. 2
   workup.STIRRINGstirred overnight at room temperature
3. 3
   FiltraciónFiltering the insoluble matter with Celite
4. 4
   Concentraciónthe solvent was concentrated under reduced pressure
5. 5
   OtroThe residue was purified on silica gel column chromatography (C-300, hexane:ethyl acetate=3:2-2:3)

Procedimiento

A toluene solution (13.8 mL, 13.8 mmols) of 1N diisobutylaluminium hydride was added to a THF solution (40 mL) of 2-ethoxycarbonyl-5-difluoromethoxypyridine (1.0 g, 4.6 mols) and stirred at 0° C. for 40 minutes. Successively sodium borohydride (174 mg, 4.6 mmols) and methanol (2 mL) were added and stirred at 0° C. for 30 minutes. Sodium sulfate decahydrate was added to the reaction liquid and stirred overnight at room temperature. Filtering the insoluble matter with Celite, the solvent was concentrated under reduced pressure. The residue was purified on silica gel column chromatography (C-300, hexane:ethyl acetate=3:2-2:3) to provide the title compound (738 mg, 87%).

Fuente