Nitromethane → Benzenepropanoic acid, b-(nitromethyl)-, methyl ester
Reaction equation
[C:1]([O:11][CH3:12])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:13]([CH3:16])([O-:15])=[O:14]>>[CH3:12][O:11][C:1](=[O:10])[CH2:2][CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:16][N+:13]([O-:15])=[O:14]Participants
3
Procedure
A solution of methyl cinnamate (4.93 g, 30.4 mmol) and teteramethylguanidine (3.99 g, 34.6 mmol) in nitromethane (30 ml) was stirred for 6 hours at 90° C. After removal of the solvent under reduced pressure, the residue was partitioned between water and ethyl acetate, and the organic layer was washed with water and brine and then dried over sodium sulfate. The organic solvents were removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=4/1) to afford 4-nitro-3-phenyl-butyric acid methyl ester (4.02 g, 59%)
Workup
- customAfter removal of the solvent under reduced pressure