Water → Pyridine, 2-methyl-5-(1-methylethoxy)-

HRID 1038537Notes

Reaction equation

HRID 1038537 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[H-].[Na+].[I-].[CH3:12][CH2:13][CH3:14].O>CN(C=O)C>[CH3:12][CH:13]([O:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1)[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydrideHCID 18513226Propane iodide2×

Product 1

HCID 13339809Pyridine, 2-methyl-5-(1-methylethoxy)-Yield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-hydroxy-2-methylpyridine (11.0 g, 100 mmol) was dissolved in N,N′-dimethylformamide (100 mL), added sodium hydride (7.2 g, 150 mmol) and 1-methylethane iodide (12 mL, 121 mmol) under ice-cold conditions, and the mixture was stirred at room temperature overnight. Then, 1-methylethane iodide (4 mL) was added, and the mixture was stirred at 60° C. for 4 hours. The reaction solution was added water, and extracted with diethylether. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and 5-(1-methylethoxy)-2-methylpyridine (12.7 g (yield 84%)) was obtained as a yellow oil.

Workup

  1. stirringthe mixture was stirred at 60° C. for 4 hours
  2. extractionextracted with diethylether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-76296fd3e96745859187816270202e0a
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

Loading…