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

HRID 1736249Notes

Reaction equation

HRID 1736249 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

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

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-34f91d6fcce6405384508bc4fc3167a9
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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