Methyl Acrylate → HCID 67145671, compound

HRID 2422208Notes

Reaction equation

HRID 2422208 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 hydrogencarbonate (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 hrs. The reaction mixture was allowed to return to room temperature and filtered. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and 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. customto return to room temperature
  2. filtrationfiltered
  3. additionWater was added
  4. extractionthe 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-58b7f920ca434c15a30ffd0d5a11d4e9
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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