(Z)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-acrylic acid ethyl ester → [Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:25])/[C:5](/[O:22][CH2:23][CH3:24])=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][C:8]=1[CH3:21])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH:5]([O:22][CH2:23][CH3:24])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:21])[CH3:2]Participants
4
Procedure
A solution of 3-(4-benzyloxy-2-methyl-phenyl)-2Z-ethoxy-acrylic acid ethyl ester (1 g, 2.9 mmol) in ethanol (50 ml) was hydrogenated over 10% palladium on charcoal (250 mg) at ambient temperature for 2 h. The catalyst was filtered off and the solvent evaporated under reduced pressure to give 600 mg (2.4 mmol, 81%) of the title compound as yellow liquid which was used in the next stage without further purification.