Isopropenyl acetate → Methyl [3-(2-oxopropyl)phenyl]acetate
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.C[O-].C([Sn+](CCCC)CCCC)CCC.C([O:31][C:32]([CH3:34])=[CH2:33])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[F-].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O>[O:31]=[C:32]([CH3:34])[CH2:33][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
A stirred mixture of methyl (3-bromophenyl)acetate (19.7 g, 86.0 mmol), tributyltin methoxide (37.1 mL, 129 mmol), isopropenyl acetate (14.2 mL, 129 mmol), palladium acetate (961 mg, 4.28 mmol), and tri-o-tolylphosphine (2.63 g, 8.64 mmol) in toluene (70 mL) was heated at 100° C. for 6 h. Aqueous potassium fluoride solution (4 M, 120 mL) and EtOAc (200 mL) were added and the resulting mixture was stirred overnight. The mixture was then filtered through Celite and the layers were separated. The organic layer was washed with water and then concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-8% MeOH in DCM) to give the title compound (11.8 g, 66% yield).
Workup
- filtrationThe mixture was then filtered through Celite
- customthe layers were separated
- washThe organic layer was washed with water
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel flash chromatography (0-8% MeOH in DCM)
Sources & evidence
- ORD record
- ord-72744b615cf0448e9207f835072a0e58
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08816088B2
Reaction notes
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