Methyl Acrylate → HCID 10130436, compound

HRID 919109Notes

Reaction equation

HRID 919109 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)=[O:3].[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].C(=O)(O)[O-].[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:2]([C:4]1[CH:9]=[CH:8][C:7](/[CH:13]=[CH:12]/[C:11]([O:15][CH3:16])=[O:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 3

HCID 7294Methyl AcrylateHCID 7466p-BromoacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 10130436HCID 10130436, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To 4-bromoacetophenone (1 g, 5 mmol) in anhydrous DMF (30 mL) were added methyl acrylate (450 μL, 5 mmol), sodium bicarbonate (420 mg, 5 mmol) tetrabutylammonium bromide (1.61 g, 5 mmol) and palladium acetate (56 mg, 0.25 mmol) and the reaction mixture was heated at 130° C. for 2 h. The DMF was removed by concentration under reduced pressure, the crude was dissolved in EtOAc (100 mL) and washed with water (100 mL) then brine (100 mL). The organic layer was dried (MgSO4), filtered and concentrated under vacuum to afford the crude product. This was purified by flash chromatography (1:1 heptane/EtOAc) to yield the desired product (784 mg, 77%). m/z=205 [M+H]+; 1H NMR (300 MHz, CDCl3) δ: 7.99 (2H, d, J=8.3 Hz), 7.73 (1H, d, J=16.2 Hz), 7.63 (2H, d, J=8.3 Hz), 6.55 (1H, d, J=16.0 Hz), 3.85 (3H, s), 2.64 (3H, s).

Workup

  1. customThe DMF was removed by concentration under reduced pressure
  2. dissolutionthe crude was dissolved in EtOAc (100 mL)
  3. washwashed with water (100 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto afford the crude product
  8. customThis was purified by flash chromatography (1:1 heptane/EtOAc)

Sources & evidence

ORD record
ord-45daad1a4d4b4cb29eb04a12ed9e9ef2
Source dataset
uspto-grants-2016_03
Patent number
US09273003B2

Reaction notes

Loading…