Methyl iodide → 4-(1-Methoxyethyl)pyridine

HRID 21372

Reaction equation

HRID 21372 reaction equation
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH3:3].[H-].[Na+].[H][H].[CH3:14]I>O1CCCC1>[CH3:14][O:1][CH:2]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90919alpha-Methyl-4-pyridinemethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 144422034-(1-Methoxyethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8.4 g (0.068 mol) of 4-(1-hydroxyethyl)pyridine in 20 ml of absolute tetrahydrofuran is added dropwise to a suspension of 2 g (0.083 mol) of sodium hydride (3.3 g of 60% oil dispersion; washed in toluene) in 80 ml of absolute tetrahydrofuran. After the development of hydrogen has ceased, 23 g (0.16 mol) of methyliodide are added at 18°-20° C. and the mixture is left to react for 2 hours. The reaction mixture is concentrated by evaporation, the residue is combined with 40% aqueous potassium carbonate solution and extracted with ether. The organic phase is separated, dried over sodium sulphate and concentrated by evaporation. After distillation of the crude product at 82°-85° C./20 mbar, 5.2 g (55.6% of theory) of the title compound are obtained.

Workup

  1. waitthe mixture is left
  2. customto react for 2 hours
  3. concentrationThe reaction mixture is concentrated by evaporation
  4. extractionextracted with ether
  5. customThe organic phase is separated
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation
  8. distillationAfter distillation of the crude product at 82°-85° C./20 mbar, 5.2 g (55.6% of theory) of the title compound
  9. customare obtained

Sources & evidence

ORD record
ord-9d0dbd675f6c4d5c966cbe879b8d52b4
Source dataset
uspto-grants-1995_06
Patent number
US05422353

Linked notes

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