Potassium Carbonate → HCID 18779701, compound

HRID 1421697Notes

Reaction equation

HRID 1421697 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.I[C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.[Cu]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([C:10]2[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 290124-Iodobenzyl alcoholHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 18779701HCID 18779701, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Chloro-2-pyridinol (0.61 g, 4.7 mmol), 4-iodobenzyl-alcohol (1.00 g, 4.27 mmol), Copper (0.27 g, 4.27 mmol) and K2CO3 (0.65 g, 4.70 mmol) were heated at 180° C. for 16 hrs. The brown reaction mixture was cooled, diluted with EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (2×) and the combined organic extracts were washed with brine, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, EtOAc as eluent) to afford the title compound as a white solid.

Workup

  1. temperatureThe brown reaction mixture was cooled
  2. washwashed with saturated NaHCO3
  3. extractionThe aqueous layer was extracted with EtOAc (2×)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed (silica gel, EtOAc as eluent)

Sources & evidence

ORD record
ord-9e27be849b9f4cd0a37ec4cd3e4689b7
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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