4-((4-Fluorophenyl)methylene)-2-methyl-5(4H)-oxazolone → 3,4,4-Trifluorobut-3-enyl 3-(4-fluorophenyl)-2-acetylamino-prop-2-enoate

HRID 612502

Reaction equation

HRID 612502 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:15])[C:5](=[CH:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:6]=1.[F:16][C:17](=[C:21]([F:23])[F:22])[CH2:18][CH2:19][OH:20]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[F:14][C:11]1[CH:10]=[CH:9][C:8]([CH:7]=[C:5]([NH:6][C:2](=[O:3])[CH3:1])[C:4]([O:20][CH2:19][CH2:18][C:17]([F:16])=[C:21]([F:23])[F:22])=[O:15])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 3670734-((4-Fluorophenyl)methylene)-2-methyl-5(4H)-oxazoloneHCID 117685733,4,4-Trifluorobut-3-en-1-ol

Product 1

HCID 541796963,4,4-Trifluorobut-3-enyl 3-(4-fluorophenyl)-2-acetylamino-prop-2-enoateYield 49.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

8.2 g (40 mmol) of 2-methyl-4-(4-fluorobenzylidene)-oxazol-5-one of Example (II-1) in 100 ml of toluene are heated overnight under reflux with 6.3 g (50 mmol) of 3,4,4-trifluorobut-3-enol, with the addition of 200 mg of 4-dimethylaminopyridine. After cooling, the solution is washed with water and concentrated under reduced pressure and the brown solid is chromatographed over silica gel using the system chloroform/ethyl acetate (4:1). 6.5 g (Yield 49% of theory) of 3,4,4-trifluorobut-3-enyl 3-(4-fluorophenyl)-2-acetylamino-prop-2-enoate of mp.: 116° are obtained.

Workup

  1. customare heated overnight
  2. temperatureAfter cooling
  3. washthe solution is washed with water
  4. concentrationconcentrated under reduced pressure
  5. customthe brown solid is chromatographed over silica gel using the system chloroform/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-c1ef2b91c0084b979560fcc2f9fcf530
Source dataset
uspto-grants-1999_12
Patent number
US06004992

Linked notes

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