methyl(2E)-3-(4-methoxy-2-nitrophenyl)acrylate → HCID 23003572, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])=[C:5]([N+:15]([O-])=O)[CH:4]=1>C(O)(=O)C.[Zn]>[NH2:15][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of methyl (2E)-3-(4-methoxy-2-nitrophenyl)acrylate (Intermediate 5, 4.9 g, 20.66 mmol) in acetic acid (150 mL) at room temperature under nitrogen was added zinc powder (7.7 g, 118 mmol) in portions. After 4 hours, another 5 g of zinc was added and the resulting reaction mixture was heated at 50° C. for two hours. The reaction mixture was then cooled to room temperature, filtered, and the filtrate was concentrated to dryness under reduced pressure. The residue was chromatographed on silica gel with hexanes/ethyl acetate (3:1) to give 1.0 g (23% yield) of product as a yellow solid, mp 149° C.
Workup
- customthe resulting reaction mixture
- temperatureThe reaction mixture was then cooled to room temperature
- filtrationfiltered
- concentrationthe filtrate was concentrated to dryness under reduced pressure
- customThe residue was chromatographed on silica gel with hexanes/ethyl acetate (3:1)
Sources & evidence
- ORD record
- ord-d79fb6bd28e349649dd80a02cb11ce72
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07875715B2
Reaction notes
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