Triethylamine → 4-Formylcinnamic acid tert-butyl ester
Reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+].[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[CH:23]=[CH2:24]>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([O:26][C:22](=[O:25])[CH:23]=[CH:24][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:30])([CH3:29])[CH3:28]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
A solution of 4-bromo benzaldehyde (2 g, 10.8 mmol) in DMF (50 ml) and triethylamine (3.4 ml, 27 mmol) was degassed flushing N2 for 30 min. PPh3 (141 mg, 0.54 mmol), Pd(OAc)2 (48.4 mg, 0.21 mmol), NaHCO3 (1.84 g, 21.6 mmol) and tert-butyl acrylate (1.58 ml, 10.8 mmol) were added and the resulting mixture was heated to reflux for 3 h. Additional Pd(OAc)2 (24 mg) was added and the mixture was heated to 100° C. for 1 h. The solution was diluted with H2O and extracted with Et2O. The organic layer was dried over Na2SO4 and the solvent was evaporated under vacuo to give the crude product that was triturated in isopropyl ether to give 1.6 g of 3-(4-formyl-phenyl)-acrylic acid tert-butyl ester.
Workup
- customflushing N2 for 30 min
- temperaturethe resulting mixture was heated
- temperatureto reflux for 3 h
- extractionextracted with Et2O
- dry with materialThe organic layer was dried over Na2SO4
- customthe solvent was evaporated under vacuo
- customto give the crude product that
- customwas triturated in isopropyl ether
Sources & evidence
- ORD record
- ord-3d8f8591fd074ba7868e16a6c640501a
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803800B2
Reaction notes
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