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

HRID 1690167Notes

Reaction equation

HRID 1690167 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). The resultant mixture was added with sodium hydride (7.2 g, 150 mmol) and 1-methylethane iodide (12 mL, 121 mmol) under ice-cold conditions, and stirred at room temperature overnight. Subsequently, 1-methylethane iodide (4 mL) was added and the resultant mixture was stirred at 60° C. for 4 hours. The reaction solution was added with water and extracted with diethyl ether. The organic layer was washed with brine, dried using sodium sulfate, and concentrated in vacuo. The obtained residue was purified using 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. extractionextracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified

Sources & evidence

ORD record
ord-bccee45b6ace4091b3bc051540bcbe38
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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