Water → 2-chloro-3-(methoxymethoxy)Pyridine

HRID 2223464Notes

Reaction equation

HRID 2223464 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:11][O:12][CH2:13]Cl.O>O1CCCC1>[Cl:3][C:4]1[C:9]([O:10][CH2:11][O:12][CH3:13])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 811362-Chloro-3-pyridinol

Product 1

HCID 574300802-chloro-3-(methoxymethoxy)PyridineYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (66%, 633 mg, 17.4 mmol) was added to an ice-cooled solution of 2-chloro-3-hydroxypyridine (2.05 g, 15.8 mmol) in tetrahydrofuran (30 ml) under nitrogen atmosphere, and this reaction mixture was stirred at that temperature for 15 minutes. Chloromethyl methyl ether (1.32 ml, 17.4 mmol) was added, and the resulting reaction mixture was stirred at that temperature for 30 minutes, then at room temperature for another 2 hours. After water was added, the reaction mixture was extracted with ethyl acetate, washed with saturated brine, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (2.44 g).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred at that temperature for 30 minutes
  3. waitat room temperature for another 2 hours
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40113e075b894dafa1486e5dae0310b2
Source dataset
uspto-grants-2008_05
Patent number
US07375204B2

Reaction notes

Loading…