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

HRID 352078

반응식

HRID 352078 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.Cl[CH2:17][C:18]([CH2:20]Cl)=O.O.O.O.C([O-])(=[O:27])C.[Na+].[OH-].[Na+]>O.C1(C)C=CC=CC=1.CS(C)=O>[OH:27][CH2:17][C:18]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:20]=1

참가 물질

8

반응물 4

HCID 107931,3-DichloroacetoneHCID 14798Sodium HydroxideHCID 57090144-(Trifluoromethyl)cinnamamideHCID 23665404Sodium Acetate Trihydrate

생성물 1

HCID 129928474-(hydroxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole수율 48%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매2회HCID 1140Toluene용매3회

반응 조건

온도
72.5 °C

실험 절차

(E)-3-(4-(Trifluoromethyl)phenyl)-2-propenamide (20.0 g, 92.9 mmol) was added to toluene (75 ml), and 1,3-dichloroacetone (22.0 g, 173.3 mmol) and toluene (25 ml) were added. The mixture was subjected to refluxing azeotropic dehydration for 9 hours. The reaction mixture was divided into two equal portions and one of them was concentrated under reduced pressure. To the residue were added dimethyl sulfoxide (100 ml), sodium acetate trihydrate (15.9 g, 116.8 mmol) and water (20 ml). The mixture was stirred at 70-75° C. for 4.5 hours. 2N-Aqueous sodium hydroxide solution (60 ml) was added at the same temperature and the mixture was stirred for 1 hour. After allowing to cool to room temperature, toluene (400 ml) and water (400 ml) were added and the mixture was partitioned. After washing with 5% brine (200 ml), the organic layer was concentrated under reduced pressure. To the residue was added methanol (10 ml) and the mixture was heated to 60° C. to allow dissolution. After allowing to cool to room temperature and stirring, the mixture was stirred for 1 hour under ice-cooling. The precipitated crystals were collected by filtration, washed with cold-methanol (5 ml) and dried under reduced pressure to give 4-(hydroxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]-ethenyl]-1,3-oxazole (5.96 g, 22.1 mmol, yield 48%).

후처리

  1. additionwere added
  2. temperatureto refluxing azeotropic dehydration for 9 hours
  3. concentrationwas concentrated under reduced pressure
  4. stirringthe mixture was stirred for 1 hour
  5. temperatureto cool to room temperature
  6. customthe mixture was partitioned
  7. washAfter washing with 5% brine (200 ml)
  8. concentrationthe organic layer was concentrated under reduced pressure
  9. additionTo the residue was added methanol (10 ml)
  10. temperaturethe mixture was heated to 60° C.
  11. dissolutiondissolution
  12. temperatureto cool to room temperature
  13. stirringstirring
  14. stirringthe mixture was stirred for 1 hour under ice-
  15. temperaturecooling
  16. filtrationThe precipitated crystals were collected by filtration
  17. washwashed with cold-methanol (5 ml)
  18. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-53d8c61a726a49a69c1f9999860c037c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743924B2

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