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Triethylamine → 2-(2,6-Difluorophenyl)-4-[(4-phenoxyphenoxy)methyl]-2-oxazoline

HRID 35929
ノート
印刷プレビュー

反応式

HRID 35929 の反応式
[NH2:1][CH:2]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1)[CH2:3][OH:4].C(N(CC)CC)C.[F:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:29]=1[C:30](Cl)=O>O1CCCC1>[F:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:29]=1[C:30]1[O:4][CH2:3][CH:2]([CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[N:1]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 194240922-Amino-3-(4-phenoxyphenoxy)propanol

生成物 1

HCID 158350962-(2,6-Difluorophenyl)-4-[(4-phenoxyphenoxy)methyl]-2-oxazoline収率 76.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of 1.14 g (4.40 mmol. ) of 2-amino- 3-(4-phenoxyphenoxy)propanol, 0.58 g (5.72 mmol.) of triethylamine and 20 ml of anhydrous tetrahydrofuran, there was added dropwise a solution of 0.78 g (4.40 mmol.) of 2,6-difluorobenzoylchloride in 10 ml of anhydrous tetrahydrofuran with stirring at a temperature of from 5° C. to 10° C. for 5 minutes. After addition, the reaction mixture was stirred at room temperature for 2 hours. The above mixture was filtrated with a filter glass to remove the resultant precipitate and the filtrate was concentrated under reduced pressure. To the residue, there was added 20 ml of toluene and 10 ml of thionyl chloride and the reaction mixture was refluxed by heating with stirring for 5 hours. The reaction mixture was cooled;to room temperature and concentrated under reduced pressure. To the residue, there was added 20 ml of methanol and further added dropwise 1 ml of a 5N aqueous solution of sodium hydroxide with stirring at a temperature of 60° C. for 5 minutes. Then the reaction mixture was stirred at the same temperature for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. To the residue, there was added 100 ml of ethyl acetate. The mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 1.28 g of 2-(2,6-difluorophenyl)-4-[(4-phenoxyphenoxy)methyl]-2-oxazoline as a colorless oily substance (nD19.1 1.5814).

後処理

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred at room temperature for 2 hours
  3. filtrationThe above mixture was filtrated with a filter glass
  4. customto remove the resultant precipitate
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residue, there was added 20 ml of toluene and 10 ml of thionyl chloride
  7. temperaturethe reaction mixture was refluxed
  8. temperatureby heating
  9. stirringwith stirring for 5 hours
  10. customwas cooled;to room temperature
  11. concentrationconcentrated under reduced pressure
  12. additionTo the residue, there was added 20 ml of methanol
  13. additionfurther added dropwise 1 ml of a 5N aqueous solution of sodium hydroxide
  14. stirringwith stirring at a temperature of 60° C. for 5 minutes
  15. stirringThen the reaction mixture was stirred at the same temperature for 5 hours
  16. concentrationconcentrated under reduced pressure
  17. additionTo the residue, there was added 100 ml of ethyl acetate
  18. washThe mixture was washed with water
  19. dry with materialdried over anhydrous magnesium sulfate
  20. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-87337155a34343438a6e1668baf922ef
出典データセット
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05411979

反応ノート

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