Hydrochloric Acid → trans-4-[1-methyl-2-phenyl-1H-indol-3-yl]-3-buten-2-one

反応式

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO[CH:19](OC)[CH2:20][C:21](=[O:23])[CH3:22].Cl>C(O)(=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:19]=[CH:20]/[C:21](=[O:23])[CH3:22])=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

実験手順

2.07 g of 1-methyl-2-phenyl-1H-indole, 1.32 g of 1,1-dimethoxy-3-butanone and 12 mL of acetic acid were mixed, then, 313 mg of 35 wt % hydrochloric acid was added into the mixture at room temperature, the added mixture was stirred for about 14 hours at the same temperature to cause a reaction. At a time point about 10 minutes after starting of stirring and reaction, blue solid precipitated to render stirring difficult. Therefore, 8 mL of acetic acid was added. After completion of the reaction, 60 mL of water was added dropwise, and the precipitated crystals were filtrated. The crystals were washed with 10 vol % methanol/water, then, dried to obtain 2.44 g of trans-4-[1-methyl-2-phenyl-1H-indol-3-yl]-3-buten-2-one (blue green solid). Yield: 89%.