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

HRID 1736249ノート

反応式

HRID 1736249 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-34f91d6fcce6405384508bc4fc3167a9
出典データセット
uspto-grants-1996_07
特許番号
US05539112

反応ノート

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