Ethyl formate → 2-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile

HRID 1833236Notes

Reaction equation

HRID 1833236 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C[O-].[Na+].[CH:17](OCC)=[O:18]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH:17]=[O:18])[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 667273,4-DimethoxybenzeneacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 164773122-(3,4-Dimethoxyphenyl)-3-oxopropanenitrileYield 78%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 3,4-dimethoxyphenyl acetonitrile (8.86 g, 50 mmol) in diethyl ether (150 mL) was added sodium methoxide (2.97 g, 55 mmol) and ethyl formate (4.04 mL, 50 mmol) in diethyl ether (50 mL) solution. The reaction mixture was stirred at room temperature for 24 hrs. A solid was precipitated. The mixture was filtered and the solid was collected and washed with diethyl ether. The solid was dissolved in water (50 mL). 10% acetic acid was then added dropwise to the solution. A white precipitation was formed and the mixture was filtered again. The while solid was washed with water and collected to afford 2-(3,4-dimethoxy-phenyl)-3-oxo-propionitrile (8.0 g, 78% yield).

Workup

  1. customA solid was precipitated
  2. filtrationThe mixture was filtered
  3. customthe solid was collected
  4. washwashed with diethyl ether
  5. dissolutionThe solid was dissolved in water (50 mL)
  6. addition10% acetic acid was then added dropwise to the solution
  7. customA white precipitation
  8. customwas formed
  9. filtrationthe mixture was filtered again
  10. washThe while solid was washed with water
  11. customcollected

Sources & evidence

ORD record
ord-c877461c4ac148b4bbf6850c27c99818
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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