Ethyl Acetate → 3-(3-Pyridinyl)-2-propenenitrile

HRID 1975471Notes

Reaction equation

HRID 1975471 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=O)[CH:15]=1.C(OCC)(=O)C>O1CCCC1.O>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]=[CH:5][C:3]#[N:4])[CH:15]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 103713-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 537301363-(3-Pyridinyl)-2-propenenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (62% oil, 10.87 g) in tetrahydrofuran (200 ml) was added successively diethyl cyanomethylphosphonate (43.25 ml) and pyridine-3-carbaldehyde (24 ml) at 0° C. Then, the reaction mixture was heated to refluxing temperature. After 5 hours the reaction mixture was poured into a mixture of ethyl acetate (1 l) and water (200 ml). The organic layer was separated, washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (600 ml) eluting with ethyl acetate to give 3-(3-pyridyl)acrylonitrile (23.9 g).

Workup

  1. temperatureThen, the reaction mixture was heated
  2. temperatureto refluxing temperature
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customgave a residue, which
  8. customwas chromatographed on silica gel (600 ml)
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-41d5268627cf41d2885bd74e24a6c625
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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