Methyl iodide → 4-(Benzyloxy)-2-methoxypyridine

HRID 1843713Notes

Reaction equation

HRID 1843713 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16]I>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 36077244-Benzyloxy-2(1H)-pyridone

Product 1

HCID 580537844-(Benzyloxy)-2-methoxypyridineYield 44%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 4-(benzyloxy)pyridin-2(1H)-one (9.92 g, 49.3 mmol), methyl iodide (4.60 mL, 74.0 mmol) and silver carbonate (13.6 g, 49.3 mmol) in chloroform (50 mL) was stirred with heating under reflux for four hours. After leaving to cool, the insoluble matter was separated by filtration and the filtrate was concentrated under reduced pressure. Then, the residue was purified by silica gel chromatography (hexane/ethyl acetate, 2:1) to obtain the title compound (4.65 g, 44%) as a pale yellow oil.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for four hours
  3. customAfter leaving
  4. temperatureto cool
  5. customthe insoluble matter was separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThen, the residue was purified by silica gel chromatography (hexane/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-1ddf388070ad46a3bc2b5bb30e1e46a1
Source dataset
uspto-grants-2015_02
Patent number
US08946264B2

Reaction notes

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