Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(6-Chloro-pyridin-3-yl)-acrylic acid methyl ester

HRID 2265930Notes

Reaction equation

HRID 2265930 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][C:12](=[O:33])[CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:10][O:11][C:12](=[O:33])[CH:13]=[CH:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 27640536-Chloropyridine-3-carbaldehyde

Product 1

HCID 719484463-(6-Chloro-pyridin-3-yl)-acrylic acid methyl esterYield 90.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 6-chloro-pyridine-3-carboxaldehyde (300 mg, 2.12 mmol) in toluene was added methyl(triphenylphosphoranylidene)acetate (708 mg, 2.12 mmol) and the solution was refluxed for 6 hrs. The reaction mixture was diluted with EtOAc and then washed three times with H2O, brine, dried. Na2SO4, filtered and concentrated under reduced pressure. The obtained residue was column-chromatographed to yield 3-(6-chloro-pyridin-3-yl)-acrylic acid methyl ester (380 mg, 90%).

Workup

  1. temperaturethe solution was refluxed for 6 hrs
  2. washwashed three times with H2O, brine
  3. customdried
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was column-chromatographed

Sources & evidence

ORD record
ord-69122c286804494eaee4d3454a7db4e4
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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