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

Reaktionsgleichung

Reaktionsgleichung von HRID 612502
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 541796963,4,4-Trifluorobut-3-enyl 3-(4-fluorophenyl)-2-acetylamino-prop-2-enoateAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c1ef2b91c0084b979560fcc2f9fcf530
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06004992

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