Water → Ethyl 2-(pyridin-3-yloxy)acetate

HRID 1248409Notes

Reaction equation

HRID 1248409 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].O>CS(C)=O>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 79713-HydroxypyridineHCID 24758Sodium hydride

Product 1

HCID 4763754Ethyl 2-(pyridin-3-yloxy)acetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (7.15 g) was added portion-wise to a stirred solution of 3-hydroxypyridine (19 g) in dry dimethylsulphoxide (100 ml) during 1 hr. Ethyl bromoacetate (33.4. g) was added during 1 h. and water (250 ml) slowly added. The solution was extracted with chloroform (3×150 ml) and the combined extracts washed with 2 N sodium carbonate (75 ml) and dried (Na2SO4). Evaporation of the solvent gave a liquid which was distilled (120°-130°/0.1 mm) to yield the title compound (8.7 g).

Workup

  1. extractionThe solution was extracted with chloroform (3×150 ml)
  2. washthe combined extracts washed with 2 N sodium carbonate (75 ml)
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent
  5. customgave a liquid which
  6. distillationwas distilled (120°-130°/0.1 mm)

Sources & evidence

ORD record
ord-3b45dc294ab546a484f302b23eea18ff
Source dataset
uspto-grants-1985_06
Patent number
US04524071

Reaction notes

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