1-Acetoxy-2-bromoethane → Ethyl 2-(pyridin-3-yloxy)acetate

HRID 352199Notes

Reaction equation

HRID 352199 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.Br[CH2:10][CH2:11][O:12][C:13](=[O:15])[CH3:14]>CN(C=O)C>[CH2:11]([O:12][C:13](=[O:15])[CH2:14][O:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)[CH3:10]

Participants

4

Reactant 2

HCID 135641-Acetoxy-2-bromoethaneHCID 667964713-Hydroxypyridine sodium salt

Product 1

HCID 4763754Ethyl 2-(pyridin-3-yloxy)acetateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxypyridine sodium salt, 6.4 g (36.0 mmol) in 200 mL of DMF was added 3.3 mL (30.0 mmol) of bromoethylacetate. The reaction mixture stirred overnight at rt. and was concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3. The mixture was washed with saturated NaHCO3, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by column chromatography using MeOH/chloroform as eluent and concentrated to dryness to give 3.8 g (70%) of the desired product as a tan oil. MS (ion spray) 182.1 (M+).

Workup

  1. concentrationand was concentrated to dryness
  2. customThe residue was partitioned between 20% isopropanol/chloroform and saturated aqueous NaHCO3
  3. washThe mixture was washed with saturated NaHCO3
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by column chromatography
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0ab8ef12555b46f58d45488e26dcce3f
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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