Methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]acrylate → methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]propionate
Reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])[CH3:7]>CO>[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH3:7]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]acrylate (330 mg) obtained in Step 2 was dissolved in methanol (10 ml), 5% rhodium-alumina (43 mg) was added, and the mixture was hydrogenated at atmospheric pressure overnight. The reaction mixture was filtered through Celite, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (291 mg).