Potassium Carbonate → 2-Vinylisonicotinonitrile

HRID 854346Notes

Reaction equation

HRID 854346 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=O)[CH:4]=1)#[N:2].[C:11](=O)([O-])[O-].[K+].[K+].O1CCOCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]=[CH2:11])[CH:4]=1)#[N:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 147614682-Formylpyridine-4-carbonitrile

Product 1

HCID 450800482-Vinylisonicotinonitrile

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-cyanopyridine-2-carboxaldehyde (0.916 g, 6.93 mmol), methyltriphenylphosphonium bromide (2.48 g, 6.93 mmol), potassium carbonate (1.2 g, 8.66 mmol), 1,4 dioxan (9.5 mL) and water (0.13 mL) was heated under reflux for 5 hours. The mixture was diluted with water (30 mL) and ethyl acetate (70 mL) and the organic layer separated. The aqueous phase was further extracted with ethyl acetate (2×40 mL), the organic fractions combined and dried over magnesium sulphate. After removing the solvent, the residue was purified by silica column chromatography using a Biotage cartridge and eluting with cyclohexane/ethyl acetate (7:3 v/v), then (1:1 v/v). This gave the title compound as an oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customthe organic layer separated
  4. extractionThe aqueous phase was further extracted with ethyl acetate (2×40 mL)
  5. dry with materialdried over magnesium sulphate
  6. customAfter removing the solvent
  7. customthe residue was purified by silica column chromatography
  8. washeluting with cyclohexane/ethyl acetate (7:3 v/v)

Sources & evidence

ORD record
ord-66a937c200a0474e83f12971aa0625b1
Source dataset
uspto-grants-2007_08
Patent number
US07259163B2

Reaction notes

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