Methyl 3-(3-(benzyloxy)phenyl)-4-methoxybut-2-enoate → Methyl 3-(3-hydroxyphenyl)-4-methoxybutanoate
Reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]([CH2:21][O:22][CH3:23])=[CH:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:15]([CH2:21][O:22][CH3:23])[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][CH:14]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 102.B (mixture of geometric isomers) (0.11 g, 0.35 mmol) in EtOAc (2 mL) was added Pd/C (10 wt. %) (0.019 g, 0.018 mmol) under N2. The mixture was purged with H2, stirred overnight under a H2 balloon, filtered through silica gel (EtOAc), and concentrated. The crude product was purified by silica gel flash chromatography (10-40% EtOAc/hexane) to afford 102.C (0.060 g, 76%) as a pale yellow oil.