Acrolein → HCID 86672787, compound
Reaction equation
[CH:1]([CH:3]=[CH2:4])=[O:2].[C:5](=O)([O-])[O-].[K+].[K+].I[C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:2]=[CH:1][CH:3]=[CH:4][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH2:18][CH3:5])=[O:16]Participants
8
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 80 °C
Procedure
Acrolein (180 μl, 2.71 mmol), tetrabutylammonium bromide (385 mg, 1.19 mmol), palladium acetate (5 mmol %) and potassium carbonate (450 mg, 3.26 mmol) were added to a solution of methyl 3-iodobenzoate (300 mg, 1.08 mmol) in DMF (6.0 ml), and the mixture was heated with stirring at 80° C. for two hours. The reaction mixture was cooled to room temperature and then diluted with ethyl acetate, and the organic layer was washed with water and saturated brine. The organic layer was concentrated under reduced pressure, and the resulting residue was then purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give ethyl 3-(3-oxoprop-1-en-1-yl)benzoate as a white solid (280 mg, 96%).
Workup
- temperaturethe mixture was heated
- temperatureThe reaction mixture was cooled to room temperature
- washthe organic layer was washed with water and saturated brine
- concentrationThe organic layer was concentrated under reduced pressure
- customthe resulting residue was then purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
Sources & evidence
- ORD record
- ord-6e6d3bc25ebe4d2483eba454bee42c67
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169254B2
Reaction notes
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