Phenol → HCID 23130433, compound

HRID 2080162Notes

Reaction equation

HRID 2080162 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][CH:7]=1.[C:14]1(O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][N:11]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 11228788(6-Methylpyridin-3-yl)methanol

Product 1

HCID 23130433HCID 23130433, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (1 mL) was added to (6-methyl-pyridin-3-yl)-methanol (300 mg, 2.44 mmol) at 0° C., and the solution was stirred at room temperature for 20 minutes. The reaction solution was partitioned in an aqueous solution of saturated sodium bicarbonate and ethyl acetate. This organic layer was separated, washed with brine, and then, dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo. N,N-dimethylformamide (5 mL), phenol (230 mg, 2.44 mmol) and potassium carbonate (674 mg, 4.88 mmol) were added to this residue at room temperature. This reaction mixture was stirred at room temperature for 40 minutes, then, further stirred for at 60° C. 40 minutes. The reaction solution was partitioned in water and ethyl acetate. The organic layer was separated, washed with water and brine, and then, dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (heptane/ethyl acetate=2/1), and the title compound (323 mg, 66%) was obtained as a white solid.

Workup

  1. customThe reaction solution was partitioned in an aqueous solution of saturated sodium bicarbonate and ethyl acetate
  2. customThis organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe organic layer was filtered
  6. customthe solvent was evaporated in vacuo
  7. stirringThis reaction mixture was stirred at room temperature for 40 minutes
  8. stirringfurther stirred for at 60° C
  9. custom40 minutes
  10. customThe reaction solution was partitioned in water
  11. customThe organic layer was separated
  12. washwashed with water and brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. filtrationThe organic layer was filtered
  15. customthe solvent was evaporated in vacuo
  16. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-34d6fd902a4d4fb594b7eae97a7031cb
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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