Ethanol → (2Z, 4E)-6-(2,5-dimethoxyphenyl)-6-oxo-3-phenylhexa-2,4-dienoic acid

反応式

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:27])/[CH:12]=[CH:13]/[C:14](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:15]/[C:16]([O:18]CC)=[O:17].C(O)C.C(=O)(O)[O-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:27])/[CH:12]=[CH:13]/[C:14](/[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[CH:15]/[C:16]([OH:18])=[O:17]

参加物

実験手順

0.45 g (1.22 mmol) of ethyl (2Z, 4E)-6-(2,5-dimethoxyphenyl)-6-oxo-3-phenylhexa-2,4-dienoate, 20 ml of ethanol, 0.206 g (2.44 mmol) of sodium bicarbonate and 20 ml of water are mixed together and refluxed for three hours. After evaporating off the solvents, the residue is poured into water, acidified with normal hydrochloric acid solution and extracted with dichloromethane. The organic phase is dried (Na2SO4), the solvent is evaporated off and the pasty product obtained is purified by flash chromatography (20/80 heptane/ethyl acetate) (yellow solid; diisopropyl ether; m.p.: 165° C.; 170 mg) and recrystallized (10/6 hexane/ethyl acetate) (0.3 g of yellow solid; 22%).