HCID 49806006, compound → HCID 68555156, compound
Reaction equation
[CH3:1][N:2]([CH3:27])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:26])[CH2:12][C:13](=[O:25])/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=2)=[CH:5][CH:4]=1>C(OCC)(=O)C.[Pd]>[CH3:27][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11](=[O:26])[CH2:12][C:13](=[O:25])[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=2)=[CH:5][CH:4]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (1E,6E)-1-(4-dimethylaminophenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (15 mg, 41 μmol, synthesized in Example 9) in 3.0 mL of ethyl acetate was added palladium 5% on carbon (30 mg) under nitrogen. After the vessel was purged with hydrogen, the reaction mixture was stirred under 1 atm of hydrogen at room temperature for 1.5 h. After the vessel was purged with nitrogen, the reaction mixture was filtered to remove palladium 5% on carbon. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=75/25 to 65/35) to obtain the title compound as a gum (8.0 mg, 53%) having the following characteristics.