Methyl 4-[2-(4-fluorophenyl)ethenyl]-3-methoxycarbonylbenzoate → Methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:4][CH:3]=1>[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[C:20]([O:22][CH3:23])=[O:21])=[CH:6][CH:7]=1Participants
4
Procedure
A mixture of methyl 4-[2-(4-fluorophenyl)ethenyl]-3-methoxycarbonylbenzoate (56.75 g, 180.6 mmol), ethyl acetate (900 ml), 10% palladium on carbon (6 g) was stirred under an hydrogen atmosphere for 6 hours. The catalyst was filtered and replaced with fresh catalyst (6 g). The reaction was then stirred under an hydrogen atmosphere for 16 hours. The catalyst was filtered and the filtrate evaporated to dryness to give as a colourless gum, methyl 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoate (55.00 g).