Reaktion #340643

Reaktionsgleichung

Methyl iodide

4-(1H-Benzimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde

4-(1H-benzimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde

N,N-dimethylformamide

sodium hydride

→

desired compound

Ausbeute 55.0%

2-fluoro-5-methoxy-4-(1-methyl-1H-benzimidazol-2-ylmethoxy)-benzaldehyde

Ausbeute 55.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred overnight at room temperature under an atmosphere of nitrogen
2. 2
   SonstigeThe solvent was evaporated to dryness under reduced pressure
3. 3
   workup.ADDITIONEthyl acetate was added
4. 4
   Waschenthe organic portion was washed with water
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigePurification with silica gel flash chromatography with a gradient of ethyl acetate in hexanes

Vorschrift

4-(1H-Benzimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde (142) (0.600 g, 2.0 mmol) was dissolved in N,N-dimethylformamide (15 mL, 190 mmol). After the addition of sodium hydride (60% dispersion in oil, 0.072 g, 3.0 mmol) the reaction was stirred for 15 minutes at room temperature. Methyl iodide (140 μL, 2.2 mmol) was added dropwise to the mixture. The reaction was stirred overnight at room temperature under an atmosphere of nitrogen. The solvent was evaporated to dryness under reduced pressure. Ethyl acetate was added and the organic portion was washed with water, dried over anhydrous sodium sulfate and concentrated. Purification with silica gel flash chromatography with a gradient of ethyl acetate in hexanes gave the desired compound as a white powder (143, 0.345 g, 55%). MS (ESI) [M+H+]+=315.2.

Quelle