Water → Tert-butyl 2-(3-pyridyloxy)acetate

HRID 2246480Notes

Reaction equation

HRID 2246480 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][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].O>CN(C=O)C>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetate

Product 1

HCID 22668053Tert-butyl 2-(3-pyridyloxy)acetateYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.22 g of sodium hydride (60% oil dispersion, 5.5 mmol) in 2 mL of DMF was added dropwise a solution of 0.48 g of 3-hydroxypyridine (5.0 mmol) in 2 mL of DMF at room temperature, and the mixture was stirred for an hour. The resulting brown solution was ice-cooled, 0.81 mL of tert-butyl bromoacetate (5.5 mmol) was added, and the mixture was stirred under ice-cooling for an hour followed by stirring at room temperature for 2 hours. After addition of water, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and evaporated. The residue was purified by column-chromatography on silica gel (eluent: chloroform:ethyl acetate=5:1), to give 0.34 g of tert-butyl 3-pyridyloxyacetate (Yield: 32.5%) as a clear oil.

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for an hour
  4. stirringby stirring at room temperature for 2 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column-chromatography on silica gel (eluent: chloroform:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-b6409f4c6bce4bd5ae05ede8e01f19d8
Source dataset
uspto-grants-2010_03
Patent number
US07687525B2

Reaction notes

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