Reaktion #165236

Reaktionsgleichung

3,4-Difluorobenzaldehyde

N,N-dimethylformamide

2-(hydroxymethyl)-pyridine

sodium hydride

→

title compound

Ausbeute 45.6%

3-Fluoro-4-(pyridin-2-ylmethoxy)-benzaldehyde

Ausbeute 45.6%

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 20 minutes at room temperature
2. 2
   Extraktionwhich was then extracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with saturated aqueous sodium chloride
4. 4
   Sonstigethe solvent was evaporated under a reduced pressure
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1→2:1)

Vorschrift

To an N,N-dimethylformamide (40.0 mL) solution of 2-(hydroxymethyl)-pyridine (3.00 g, 27.5 mmol) was added sodium hydride (1.00 g, 25.0 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 20 minutes at room temperature. 3,4-Difluorobenzaldehyde (4.69 g, 33.0 mmol) was then added at 0° C., and stirred for 20 minutes at room temperature. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:1→2:1) to obtain the title compound (2.90 g, 45.6%).

Quelle