Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 68786094, compound

HRID 2265964Notes

Reaction equation

HRID 2265964 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:4]=1.[CH3:15][O:16][C:17](=[O:38])[CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH3:15][O:16][C:17](=[O:38])[CH:18]=[CH:9][C:6]1[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 866255266-Methoxy-4-(trifluoromethyl)-3-pyridinecarboxaldehyde

Product 1

HCID 68786094HCID 68786094, compoundYield 73.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-methoxy-4-trifluoromethyl-3-pyridinecarboxaldehyde (150 mg, 0.73 mmol) in toluene (8 mL) was added methyl(triphenylphosphoranylidene)acetate (270 mg, 0.81 mmol). The mixture was heated at 110° C. for overnight, cooled to room temperature, and diluted with EtOAc and water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc/hexanes=1/4) to give 3-(6-methoxy-4-trifluoromethylpyridin-3-yl)-acrylic acid methyl ester (140 mg, 73.3%) as a mixture of cis- and trans-isomers (cis-/trans-=1/10). The trans-isomer was then isolated by recrystallization from hexanes to give 60 mg as a solid.

Workup

  1. temperaturecooled to room temperature
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (EtOAc/hexanes=1/4)

Sources & evidence

ORD record
ord-19ee21ba87dc45a9b652b290f647b27a
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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