Sodium Methoxide → 4-Chloro-2-(methoxymethyl)pyridine

HRID 2086257Notes

Reaction equation

HRID 2086257 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9]Cl)[CH:4]=1.[CH3:11][O-:12].[Na+]>CO>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][O:12][CH3:11])[CH:4]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 227272744-Chloro-2-(chloromethyl)pyridine--hydrogen chloride (1/1)

Product 1

HCID 227270924-Chloro-2-(methoxymethyl)pyridineYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-chloro-2-chloromethylpyridine hydrochloride (0.43 g), sodium methoxide (1.11 g) and methanol (15 ml) was stirred at room temperature for 10 hours and at 70° C. for 7 hours. The reaction mixture was concentrated, and the residue was combined with water and methylene chloride, and the organic phase was separated. After washing with saturated aqueous sodium bicarbonate followed by drying and concentrating, a title compound (0.28 g) was obtained as a tan oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe organic phase was separated
  3. washAfter washing with saturated aqueous sodium bicarbonate
  4. customby drying
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-01b252892f29416aba673e6e2f47436c
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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