Chloromethyl Methyl Ether → 2-chloro-5-(MethoxyMethoxy)pyridine

HRID 2207285Notes

Reaction equation

HRID 2207285 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:12][O:13][CH3:14]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:12][O:13][CH3:14])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 587641932-chloro-5-(MethoxyMethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1000 mg (1 eq) of 6-chloropyridin-3-ol was dissolved in 50 mL of N,N-dimethylformamide, and 370 mg (1.2 eq) of sodium hydride was added thereto, followed by stirring at room temperature for 1 hour. Then, 688 uL (1.1 eq) of chloro(methoxy)methane was added slowly thereto, and the solution was stirred at room temperature for 2 hours. N,N-dimethylformamide was removed by concentrating under reduced pressure. After extracting with ethyl acetate, the extract was treated with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=9:1) to obtain 1200 mg of 2-chloro-5-(methoxymethoxy)pyridine.

Workup

  1. stirringthe solution was stirred at room temperature for 2 hours
  2. customN,N-dimethylformamide was removed
  3. concentrationby concentrating under reduced pressure
  4. extractionAfter extracting with ethyl acetate
  5. additionthe extract was treated with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated by column chromatography (developing solvent, hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-658069f554704a9486a742f4964dbd22
Source dataset
uspto-grants-2016_06
Patent number
US09376429B2

Reaction notes

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