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

HRID 352072

反応式

HRID 352072 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.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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒

反応条件

温度
72.5 °C

実験手順

(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%).

後処理

  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

出典と根拠

ORDレコード
ord-6c7a09e552c3430f98ac75e781c5f0fa
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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