Methyl iodide → 2-Chloro-5-(methoxymethyl)pyridine

HRID 1753798Notes

Reaction equation

HRID 1753798 reaction equation
[CH3:1]C([O-])(C)C.[K+].[Cl:7][C:8]1[N:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.IC>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][O:15][CH3:1])=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 177161(6-Chloropyridin-3-yl)methanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 190109212-Chloro-5-(methoxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.6 g (23.0 mmol) potassium tert-butylate are dissolved in 50 ml THF. 3.0 g (20.9 mmol) (6-chloropyridin-3-yl)methanol are added and the mixture is stirred at RT for 15 min 4.4 g (31.3 mmol) iodomethane are then added and the mixture is stirred for approx. 30 min until the slightly exothermic reaction has subsided. The solvent is removed, the residue is taken up in methylene chloride and the mixture is washed twice with water. The mixture is dried over magnesium sulfate and concentrated and the residue is purified by column chromatography over silica gel (Biotage chromatography, mobile phase: cyclohexane/ethyl acetate 85:15).

Workup

  1. additionare then added
  2. customThe solvent is removed
  3. washthe mixture is washed twice with water
  4. dry with materialThe mixture is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue is purified by column chromatography over silica gel (Biotage chromatography, mobile phase: cyclohexane/ethyl acetate 85:15)

Sources & evidence

ORD record
ord-a1e0e17ad78348db9e7f0821792424f0
Source dataset
uspto-grants-2015_10
Patent number
US09168249B2

Reaction notes

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