Water → HCID 54291565, compound
Reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:16])[CH2:7]P(OCC)(OCC)=O)[CH3:4].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[C:27]([N+:33]([O-:35])=[O:34])[CH:26]=2)[CH:20]=1.O>O1CCCC1>[CH2:3]([O:5][C:6](=[O:16])[CH:7]=[CH:29][C:28]1[CH:31]=[CH:32][C:25]([C:21]2[CH:20]=[C:19]([O:18][CH3:17])[CH:24]=[CH:23][N:22]=2)=[CH:26][C:27]=1[N+:33]([O-:35])=[O:34])[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To a suspension of sodium hydride (60% dispersion in mineral oil, 101 mg) in tetrahydrofuran (10 ml) was added a solution of diethylphosphonoacetic acid ethyl ester (0.535 ml) dropwise at 0° C., and the mixture was stirred at 5° C. for 30 minutes. Then to the resultant mixture was added a solution of 4-(4-methoxypyridin-2-yl)-2-nitrobenzaldehyde (543 mg) in tetrahydrofuran (10 ml) dropwise at 0° C., and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, filtered and dried to give 4-(4-methoxypyridin-2-yl)-2-nitrocinnamic acid ethyl ester (557 mg).
Workup
- stirringthe mixture was stirred at ambient temperature for 1 hour
- extractionextracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- customevaporated under reduced pressure
- customThe residue was triturated with diisopropyl ether
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-19f6fb3203644195a2d93500a6cad4a5
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06521643B1
Reaction notes
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