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Triethylamine → 2-(2,6-Diflurophenyl)-4-{[4-(1,1-dimethylethyl)phenoxy]methyl}-2-oxazoline

HRID 35927
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HRID 35927 반응식
[NH2:1][CH:2]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1)[CH2:3][OH:4].C(N(CC)CC)C.[F:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:26]=1[C:27](Cl)=O>O1CCCC1>[F:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:26]=1[C:27]1[O:4][CH2:3][CH:2]([CH2:5][O:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][CH:12]=2)[N:1]=1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 152799222-Amino-3-[4-(1,1-dimethylethyl)phenoxy]propanol

생성물 1

HCID 152799232-(2,6-Diflurophenyl)-4-{[4-(1,1-dimethylethyl)phenoxy]methyl}-2-oxazoline수율 76.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a mixture of 1.46 g (6.54 mmol.) of 2-amino-3-[4-(1,1-dimethylethyl)phenoxy]propanol, 0.86 g (8.50 mmol.) of triethylamine and 20 ml of anhydrous tetrahydrofuran, there was added dropwise a solution of 1.15 g (6.54 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 one hour. After the reaction was completed, the resultant mixture was concentrated under reduced pressure. To the residue, there was added 20 ml of benzene and 10 ml of thionyl chloride and the reaction mixture was refluxed by heating with stirring for 3 hours. Then the reaction mixture was cooled to room temperature and concentrated under reduced pressure. To the residue, there was added 20 ml of ethanol and further added dropwise 1.4 ml of a 5N aqueous solution of sodium hydroxide with stirring at a temperature of 60° C. for 5 minutes. The reaction mixture was then stirred at the same temperature for 3 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 1.72 g of 2-(2,6-diflurophenyl)-4-{[4 -(1,1-dimethylethyl)phenoxy]methyl}-2-oxazoline as a colorless oily substance (nD19.1 1.5391).

후처리

  1. additionAfter addition
  2. stirringthe reaction mixture was stirred at room temperature for one hour
  3. concentrationthe resultant mixture was concentrated under reduced pressure
  4. additionTo the residue, there was added 20 ml of benzene and 10 ml of thionyl chloride
  5. temperaturethe reaction mixture was refluxed
  6. temperatureby heating
  7. stirringwith stirring for 3 hours
  8. concentrationconcentrated under reduced pressure
  9. additionTo the residue, there was added 20 ml of ethanol
  10. additionfurther added dropwise 1.4 ml of a 5N aqueous solution of sodium hydroxide
  11. stirringwith stirring at a temperature of 60° C. for 5 minutes
  12. stirringThe reaction mixture was then stirred at the same temperature for 3 hours
  13. temperaturethe reaction mixture was cooled to room temperature
  14. concentrationconcentrated under reduced pressure
  15. additionTo the residue, there was added 100 ml of ethyl acetate
  16. washThe mixture was washed with water
  17. dry with materialdried over anhydrous magnesium sulfate
  18. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8104bc391538467eab96ee068dd11b8d
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05411979

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