반응 #91984

반응 방정식

water

2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-N-methoxy-N-methyl-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carboxamide

lithium aluminum hydride

ammonium chloride

→

title compound

수율 103.7%

2-(Ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carbaldehyde

수율 103.7%

용매

ethyl acetate

THF

THF

반응 조건

후처리

1. 1
   기타The phases were separated
2. 2
   추출the water layer was extracted with ethyl acetate (30 mL)
3. 3
   세척the organic phases were washed with water (20 mL)
4. 4
   건조dried with MgSO4
5. 5
   농축concentrated in vacuo

실험 절차

To a solution of 2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-N-methoxy-N-methyl-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carboxamide (520 mg, 808 μmol) in THF (7 mL) in an inert atmosphere was added with stirring at 0° C. a solution of lithium aluminum hydride in THF (1 M, 404 μl, 404 μmol). The mixture was stirred 1 h at 0° C., saturated ammonium chloride solution (10 mL) was added slowly and finally water (20 mL) and ethyl acetate (30 mL) were added. The phases were separated, the water layer was extracted with ethyl acetate (30 mL), and the organic phases were washed with water (20 mL), combined, dried with MgSO4, and concentrated in vacuo to give the title compound (0.49 g, quant.) as white foam (LC-MS (UV peak area, ESI) 83%, 585.4 (MH+)) that was used in the next step without further purification.

출처