Isopropenyl acetate → Methyl [3-(2-oxopropyl)phenyl]acetate

HRID 1039818Notes

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>[CH3:12][O:11][C:9](=[O:10])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH2:33][C:32](=[O:31])[CH3:34])[CH:3]=1

Participants

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-c7e970c23b244de0bfc27f5882dedfa7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551978B2

Reaction notes

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