Reaktion #521161

Reaktionsgleichung

2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethanol

sodium hydride

benzyl 3-bromopropyl ether

→

1-{2-[3-(benzyloxy)propoxy]ethyl}-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline

Ausbeute 29.0%

Lösungsmittel

N,N-dimethylformamide

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was maintained for 2 hours
2. 2
   Sonstigequenched
3. 3
   workup.ADDITIONby pouring over ice
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic fractions were washed with water
6. 6
   Trocknendried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe crude product was purified by flash column chromatography (silica gel, 4:1 ethyl acetate/hexanes)

Vorschrift

A solution of 2-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethanol (1.0 g, 3.7 mmol) in N,N-dimethylformamide was added dropwise to a suspension of sodium hydride (0.19 g of a 60% dispersion in mineral oil, 4.8 mmol) in N,N-dimethylformamide (20 ml). The reaction was maintained for 2 hours followed by the dropwise addition of benzyl 3-bromopropyl ether (0.72 ml, 4.1 mmol). The reaction was stirred overnight at 100° C., quenched by pouring over ice, and extracted with ethyl acetate. The organic fractions were washed with water, dried (MgSO4), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 4:1 ethyl acetate/hexanes) to provide 0.45 g of 1-{2-[3-(benzyloxy)propoxy]ethyl}-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinoline as a brown oil.

Quelle