Methyl Acrylate → HCID 70161444, compound

HRID 2297735Notes

Reaction equation

[CH:1](/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1Br)=[CH:2]\[CH3:3].[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH:1](/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]=[CH:12][C:11]([O:15][CH3:16])=[O:14])=[CH:2]\[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Under an argon atmosphere, 2-((E)-1-propenyl)bromobenzene (2.1 g, 11.0 mmol), methyl acrylate (4.5 mL, 50 mmol) and triethylamine (1 mL) were added to a solution (15 mL) of palladium (II) diacetate (11 mg, 0.05 mmol) and tris(2-methylphenyl)phosphine (60 mg, 0.2 mmol) in N,N-dimethylformamide, followed by stirring at 80° C. for 1 hour. Next, the reaction solution was filtered through Florisil, and the solvent contained in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with ethyl acetate/hexane=1/10) to give methyl 2-((E)-1-propenyl)cinnamate (740 mg, yield 34%).

Workup

filtrationNext, the reaction solution was filtered through Florisil
customwas evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluted with ethyl acetate/hexane=1/10)

Sources & evidence

ORD record: ord-f14444c8e00940a1be828ee5f3244c2a
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492392B1

Reaction notes

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