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

HRID 352073

反応式

HRID 352073 の反応式
[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.[C:29]([O-:32])(=[O:31])[CH3:30].[Na+]>CO.CS(C)=O>[C:29]([O:32][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:31])[CH3:30]

参加物

7

反応物 4

HCID 1140TolueneHCID 107931,3-DichloroacetoneHCID 517045Sodium AcetateHCID 57090144-(Trifluoromethyl)cinnamamide

生成物 1

HCID 129928464-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole収率 51%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒

反応条件

温度
75 °C

実験手順

(E)-3-(4-(Trifluoromethyl)phenyl)-2-propenamide (950 g, 4.42 mol) and 1,3-dichloroacetone (1045 g, 8.23 mol)were added to toluene (4.75 L) and the mixture was subjected to refluxing azeotropic dehydration using a Dean-Stark tube for 8 hours. During the reaction, an azeotropic mixture (2.38 L) was removed. The reaction mixture was concentrated under reduced pressure, and dimethyl sulfoxide (4.75L) and sodium acetate (905 g, 11.0 mol) were added to the residue. The mixture was stirred at 70-80° C. for 3.5 hours. Methanol (4.75 L) was added. 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 (1.9 L), and dried under reduced pressure to give 4-(acetoxymethyl)-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (1560 g, yield 51%).

後処理

  1. temperatureto refluxing azeotropic dehydration
  2. customfor 8 hours
  3. customDuring the reaction
  4. customan azeotropic mixture (2.38 L) was removed
  5. additionwere added to the residue
  6. temperatureto cool to room temperature
  7. stirringstirring
  8. stirringthe mixture was stirred for 1 hour under ice-
  9. temperaturecooling
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with cold-methanol (1.9 L)
  12. customdried under reduced pressure

出典と根拠

ORDレコード
ord-87acf2d9cbc24512b9fdde5a0a549b33
出典データセット
uspto-grants-2004_06
特許番号
US06743924B2

関連ノート

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