Potassium Carbonate → HCID 90202452, compound

HRID 929756Notes

Reaction equation

HRID 929756 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Cl>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 119062-Chlorobenzyl chlorideHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 90202452HCID 90202452, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

5-Hydroxy-2-methylpyridine (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 5.00 g, 45.8 mmol) was dissolved in DMF (90 mL) and K2CO3 (6.9 g, 50 mmol) and tetrabutylammonium iodide (2 g, 5.4 mmol) were added. 2-Chlorobenzyl chloride (6.4 mL, 50.6 mmol) was added and the mixture was stirred at room temperature for 20 h. The reaction mixture was partitioned between EtOAc (300 mL) and H2O (300 mL). The organic layer was dried (Na2SO4), filtered, evaporated, and purified by chromatography (30% EtOAc/hexane) to give 5-(2-chloro-benzyloxy)-2-methyl-pyridine (7.00 g, 66%) as a yellow oil.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (300 mL) and H2O (300 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by chromatography (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-7a244aec164c438c8fbb1ee39f38f67f
Source dataset
uspto-grants-2016_03
Patent number
US09296711B2

Reaction notes

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