3-Hydroxypyridine → Methyl 2-(pyridin-3-yloxy)acetate

HRID 2108126Notes

Reaction equation

HRID 2108126 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[CH:4]=1.Br[CH2:11][C:12]([O:14][CH3:15])=[O:13]>C1COCC1>[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:4]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 23008475Methyl 2-(pyridin-3-yloxy)acetateYield 22.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (3.78 g, 80% suspension in oil) was added to a solution of 3-pyridinol (10 g) in THF (150 ml) at 0°. The mixture was stirred under nitrogen for 30 min, treated dropwise with methyl bromoacetate (19.3 g), heated under reflux for 24 h, poured into ice-water (200 ml) and extracted with ethyl acetate (2×100 ml). The combined organic extracts were dried and concentrated to give an oil which was purified by FCC, eluting with System G (98:2:1) to give the title compound (4 g), as an oil. T.l.c. (System E 80:20:1) Rf 0.46

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 h
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customto give an oil which
  7. customwas purified by FCC
  8. washeluting with System G (98:2:1)

Sources & evidence

ORD record
ord-3d2cfca3e84c4fe9875d4dd96267a847
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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