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

반응식

HRID 612502 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c1ef2b91c0084b979560fcc2f9fcf530
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06004992

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