3,4-dihydro-2H-pyran → 2,3,4-trifluoro-5-pivaloylamino-O-tetrahydropyranylphenol

HRID 1736249노트

반응식

HRID 1736249 반응식
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][C:3]=1[OH:17].[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([NH:10][C:11](=[O:16])[C:12]([CH3:14])([CH3:13])[CH3:15])=[CH:4][C:3]=1[O:17][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][O:18]1

참가 물질

6

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 194349822,3,4-Trifluoro-5-pivaloylaminophenol

생성물 1

HCID 867496582,3,4-trifluoro-5-pivaloylamino-O-tetrahydropyranylphenol수율 78.3%

시약·촉매·용매 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-촉매HCID 6344Dichloromethane용매

실험 절차

1.19 g (4.82 mmol) of the above 2,3,4-trifluoro-5-pivaloylaminophenol was dissolved in 50 mL of dichloromethane, 0.88 mL (9.6 mmol) of 3,4-dihydro-2 H-pyran and 22 mg (0.095 mmol) of dl-camphorsulfonic acid were added and the mixture was stirred at room temperature for 1 hour. The reaction solution was poured into 100 mL of a 10% aqueous solution of potassium carbonate and the mixture was extracted once with chloroform. The organic layer was washed once with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was triturated with n-hexane to give 1.25 g of 2,3,4-trifluoro-5-pivaloylamino-O-tetrahydropyranylphenol (yield: 78%).

후처리

  1. extractionthe mixture was extracted once with chloroform
  2. washThe organic layer was washed once with an aqueous saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was triturated with n-hexane

출처 및 근거

ORD 기록
ord-34f91d6fcce6405384508bc4fc3167a9
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05539112

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