Réaction #43324

Équation de réaction

toluene

diisobutylaluminium hydride

2-ethoxycarbonyl-5-difluoromethoxypyridine

sodium borohydride

Sodium sulfate decahydrate

→

title compound

Rendement 87.0%

5-difluoromethoxy-2-hydroxymethylpyridine

Rendement 87.0%

Solvants

THF

methanol

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source