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

HRID 1913181Notes

Reaction equation

HRID 1913181 reaction equation
[CH3:1]C(C)([O-])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) of potassium tert-butoxide are dissolved in 50 ml of THF. 3.0 g (20.9 mmol) of (6-chloropyridin-3-yl)methanol are added, and the mixture is stirred at RT for 15 min. 4.4 g (31.3 mmol) of iodomethane are then added slowly, and the mixture is stirred for about 30 min until the slightly exothermic reaction has subsided. The solvent is removed, and the residue is taken up in dichloromethane and washed twice with water. The organic phase is dried over magnesium sulfate and concentrated, and the residue is purified by column chromatography on silica gel (Biotage chromatography, mobile phase: cyclohexane/ethyl acetate 85:15).

Workup

  1. stirringthe mixture is stirred for about 30 min until the slightly exothermic reaction
  2. customThe solvent is removed
  3. washwashed twice with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue is purified by column chromatography on silica gel (Biotage chromatography, mobile phase: cyclohexane/ethyl acetate 85:15)

Sources & evidence

ORD record
ord-6fb9a54992f846788acca02b8960c43c
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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