Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 68784038, compound

HRID 2266022Notes

Reaction equation

HRID 2266022 reaction equation
[CH2:1]([C:3]1[C:8]([CH:9]=O)=[CH:7][CH:6]=[C:5]([C:11]([F:14])([F:13])[F:12])[N:4]=1)[CH3:2].[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:8]1[C:3]([CH2:1][CH3:2])=[N:4][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86625534HCID 86625534, compound

Product 1

HCID 68784038HCID 68784038, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-ethyl-6-trifluoromethyl-pyridine-3-carbaldehyde in toluene (10 mL) was added methyl(triphenylphosphoranylidene)acetate (172 mg, 0.516 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 crude residue was purified by column chromatography (EtOAc/hexanes=1/4) to yield the 3-(2-ethyl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid methyl ester (89 mg, 80%).

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 crude residue was purified by column chromatography (EtOAc/hexanes=1/4)

Sources & evidence

ORD record
ord-79c5ce0874a842cbbb3ff1c8be3536ed
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

Loading…