3-[2-(ethoxycarbonyl)ethyl]-N-(3-pyridyl)indole → 3-(2-formylethyl)-N-(3-pyridyl)indole

反応式

C([O:3][C:4]([CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[CH:4]([CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=1)=[O:3]

参加物

実験手順

A solution of 2.7 g of 3-[2-(ethoxycarbonyl)ethyl]-N-(3-pyridyl)indole in 50 ml of dry methylene chloride under nitrogen is cooled to -75° and 10.6 ml of 1.75M diisobutylaluminum hydride in toluene is added dropwise. The reaction is stirred for 8 minutes and quenched with 10 ml of water at -75°. Cooling is stopped and the layers are separated. The organic phase is washed with water, dried over potassium carbonate and evaporated to a solid which is recrystallized from ether-hexane to yield 3-(2-formylethyl)-N-(3-pyridyl)indole, m.p. 44°-45°.