Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 66917169, compound

HRID 238326Notes

Reaction equation

HRID 238326 reaction equation
[C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3]CC)=[O:2].[F:26][C:27]([F:43])([F:42])[C:28]([NH:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[O:38][CH2:39][CH2:40][CH3:41])=O>C1(C)C=CC=CC=1>[F:26][C:27]([F:43])([F:42])[C:28]([NH:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[O:38][CH2:39][CH2:40][CH3:41])=[CH:6][C:1]([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 86641935HCID 86641935, compound

Product 1

HCID 66917169HCID 66917169, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Carboethoxymethylene triphenylphosphorane (41.52 g, 119.2 mmol) was added to a toluene solution (100 ml) of 2,2,2-trifluoro-N-(5-fluoro-2-propoxyphenyl)acetamide (15.83 g, 59.1 mmol). The mixture was stirred under a nitrogen atmosphere while heating under reflux for 4 hours. The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1). The purified product was concentrated under reduced pressure to thereby obtain 19.7 g of oily yellow ethyl ester of 4,4,4-trifluoro-3-(5-fluoro-2-propoxyphenylamino)buta-2-enoic acid (yield: 99%).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 4 hours
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was then purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)
  5. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-43559c55530e442299e5b6260722dab3
Source dataset
uspto-grants-2014_02
Patent number
US08642619B2

Reaction notes

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