3,4-dihydro-2H-pyran → HCID 11809161, compound

HRID 1736240Notes

Reaction equation

HRID 1736240 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[OH:16].[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:10](=[O:15])[C:11]([CH3:12])([CH3:13])[CH3:14])=[CH:4][C:3]=1[O:16][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][O:17]1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 15818877HCID 15818877, compound

Product 1

HCID 11809161HCID 11809161, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.15 g (9.39 mmol) of the resulting 2,4-difluoro-5-pivaloylaminophenol was dissolved in 40 ml of dichloromethane, 4.3 ml of 3,4-dihydro-2H-pyrane and 44 mg of camphorsulfonic acid were added and the mixture was stirred at room temperature for 4.3 hours. The reaction solution was added to a 5% aqueous solution of potassium carbonate and the mixture was extracted with chloroform. The organic layer was washed once with water and once with an aqueous saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent Was distilled off under reduced pressure and the residue was triturated with n-hexane to give 2.51 g (85%) of 2,4-difluoro-5-pivaloylamino-O-(2-tetrahydropyranyl)phenol.

Workup

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

Sources & evidence

ORD record
ord-fa13999c6a224c988d7a1716c5c528fa
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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