Phenol → HCID 136502901, compound

HRID 930876Notes

Reaction equation

HRID 930876 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[C:16]2[CH:17]=[C:18]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:19](COCC[Si](C)(C)C)[C:15]=2[C:14](=[O:33])[N:13]([CH3:34])[N:12]=1.[C:35]1([OH:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:34][N:13]1[C:14](=[O:33])[C:15]2[NH:19][C:18]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:17][C:16]=2[C:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[O:41][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:12]1

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 89657631HCID 89657631, compound

Product 1

HCID 136502901HCID 136502901, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Example 74f (0.26 g, 0.53 mmol), phenol (0.060 g, 0.64 mmol) and cesium carbonate (0.21 g, 0.63 mmol) in dimethylsulfoxide (5 mL) was heated at 110° C. for 6 hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was then treated with 15 mL of ethanol and 1 mL of concentrated H2SO4. The mixture was heated under reflux overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 40-80% ethyl acetate to afford 0.14 g (61%) of the title compound.

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with additional ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe residue was then treated with 15 mL of ethanol and 1 mL of concentrated H2SO4
  8. temperatureThe mixture was heated
  9. temperatureunder reflux overnight
  10. temperatureThe reaction mixture was cooled to room temperature
  11. custompartitioned between ethyl acetate and water
  12. washThe organic layer was washed with brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customThe residue was purified by flash chromatography on silica gel eluting with 40-80% ethyl acetate

Sources & evidence

ORD record
ord-383d4982e8814b1f999046c754f9059e
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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