Toluene → 4-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole

HRID 352072

반응식

HRID 352072 반응식
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.ClCC(CCl)=O.[C:22]1([CH3:28])[CH:27]=CC=CC=1.O.O.O.[C:32]([O-:35])(=[O:34])[CH3:33].[Na+]>CO.CS(C)=O>[C:32]([O:35][CH2:28][C:22]1[N:13]=[C:11](/[CH:10]=[CH:9]/[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=2)[O:12][CH:27]=1)(=[O:34])[CH3:33]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 107931,3-DichloroacetoneHCID 57090144-(Trifluoromethyl)cinnamamideHCID 23665404Sodium Acetate Trihydrate

생성물 1

HCID 129928464-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole수율 65%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 887Methanol용매

반응 조건

온도
72.5 °C

실험 절차

(E)-3-(4-(Trifluoromethyl)phenyl)-2-propenamide (10.0 g,46.5 mmol) and 1,3-dichloroacetone (11.0 g, 86.6 mmol) were added to toluene (50 ml), and the mixture was subjected to refluxing azeotropic dehydration using a Dean-Stark tube for 8.5 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added dimethyl sulfoxide (50 ml) and sodium acetate trihydrate (15.8 g, 116.1 mmol). The mixture was stirred at 70-75° C. for 4 hours. Methanol (50 ml) was added. After allowing-to cool to room temperature and stirring; the mixture was stirred under ice-cooling for 1 hour. The precipitated crystals were collected by filtration, washed with cold-methanol (30 ml) and dried under reduced pressure to give 4-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (13.1 g, yield 65%).

후처리

  1. temperatureto refluxing azeotropic dehydration
  2. customfor 8.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. temperatureAfter allowing-to cool to room temperature
  5. stirringstirring
  6. stirringthe mixture was stirred under ice-
  7. temperaturecooling for 1 hour
  8. filtrationThe precipitated crystals were collected by filtration
  9. washwashed with cold-methanol (30 ml)
  10. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-6c7a09e552c3430f98ac75e781c5f0fa
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743924B2

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