Sodium Iodide → Ethyl 4-[(6-chloro-3-pyridinyl)methoxy]benzoate

HRID 230770Notes

Reaction equation

HRID 230770 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16]Cl)=[CH:12][N:11]=1.[OH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=1>O.CN(C=O)C>[Cl:9][C:10]1[N:11]=[CH:12][C:13]([CH2:16][O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:24]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 60425518Ethyl 4-[(6-chloro-3-pyridinyl)methoxy]benzoateYield 96.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.3 g) and sodium iodide (93 mg) were added to a DMF solution (20 mL) of 2-chloro-5-chloromethylpyridine (1.0 g) and ethyl 4-hydroxybenzenecarboxylate (1.0 g), and stirred overnight at room temperature. Water was added to the reaction solution, and extracted with diethyl ether. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated off under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/2) to obtain the entitled compound (1.7 g).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=9/1 to 3/2)

Sources & evidence

ORD record
ord-0c07bf5e10514e97b0e18aca64d0f06b
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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