Iodoethane → 5-Ethoxy-2-methyl-pyridine

HRID 1650106Notes

Reaction equation

HRID 1650106 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1.[CH2:11](I)[CH3:12]>CN(C)C=O.O>[CH2:11]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)[CH3:12]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydride

Product 1

HCID 5731985-Ethoxy-2-methyl-pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 16.6 g sodium hydride in 500 ml dry dimethylformamide (DMF) under nitrogen at 0° C. is added 90 g 5-hydroxy-2-methylpyridine at such a rate that the temperature remains between 0°-5° C. When gas evolution ceases, 73.8 ml ethyl iodide in 100 ml DMF is added dropwise. After stirring at room temperature overnight, the mixture is diluted with water and extracted with ether. The ether extracts are washed with brine, dried and concentrated. This oil is distilled to give 62.5 g of 5-ethoxy-2-methylpyridine, bp 89°-91° C. at 12 mm.

Workup

  1. customremains between 0°-5° C
  2. extractionextracted with ether
  3. washThe ether extracts are washed with brine
  4. customdried
  5. concentrationconcentrated
  6. distillationThis oil is distilled

Sources & evidence

ORD record
ord-4e5f00fc021d4814a3d6be8286b2b3f6
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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