Water → 5-[1-(Methoxymethoxy)ethyl]-2-methylpyridine

HRID 1756629Notes

Reaction equation

HRID 1756629 reaction equation
[H-].[Na+].[OH:3][CH:4]([C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[N:10][CH:11]=1)[CH3:5].[CH3:13][O:14][CH2:15]Cl.O>CN(C)C=O>[CH3:13][O:14][CH2:15][O:3][CH:4]([C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[N:10][CH:11]=1)[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 101299891-(6-Methylpyridin-3-yl)ethan-1-ol

Product 1

HCID 107025455-[1-(Methoxymethoxy)ethyl]-2-methylpyridineYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride in oil (60%, 7.0 g) was added with ice-cooling to a solution of 5-(1-hydroxyethyl)-2-methylpyridine (20.0 g) in N,N-dimethylformamide (120 ml). The mixture was stirred for 15 minutes. Then, chloromethyl methyl ether (14.1 g) was added dropwise at the same temperature. The reaction mixture was further stirred for 30 minutes with ice-cooling. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and subjected to distillation under reduced pressure to obtain 5-(1-methoxymethoxyethyl)-2-methylpyridine (21.5 g, yield: 81%), b.p. 78°-80° C./0.8 mmHg.

Workup

  1. stirringThe reaction mixture was further stirred for 30 minutes with ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-f32f9947a4ca48cd8c60a0312d3cb587
Source dataset
uspto-grants-1995_08
Patent number
US05441971

Reaction notes

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