Methyl Acrylate → HCID 67145671, compound

HRID 1678569Notes

Reaction equation

HRID 1678569 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH:7]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8]2)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25]>CN(C)C=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:15][CH:7]1[O:6][C:5]1[CH:16]=[CH:17][C:2](/[CH:25]=[CH:24]/[C:23]([O:27][CH3:28])=[O:26])=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 516892Sodium BicarbonateHCID 23082968HCID 23082968, compound

Product 1

HCID 67145671HCID 67145671, compoundYield 69.4%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(4-bromophenoxy)-2,3-dihydro-1H-indene (1.4 g, 4.7 mmol) in N,N-dimethylformamide (4.7 mL) were added sodium hydrogen carbonate (1.0 g, 12 mmol), methyl acrylate (0.86 mL, 9.5 mmol), tetrabutylammonium chloride (2.0 g, 7.1 mmol) and palladium acetate (31 mg, 0.14 mmol), and the mixture was stirred at 100° C. for 24 hours. The reaction solution was returned to room temperature, and then filtered. Water was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate-hexane to give the title compound (0.96 g, yield 69%).

Workup

  1. customwas returned to room temperature
  2. filtrationfiltered
  3. additionWater was added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7509d733164d496a8f12b3e4be20b05c
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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