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

HRID 2112355Notes

Reaction equation

HRID 2112355 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) is 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-95e10a36cbf44820a7cbecf8f2ad9346
Source dataset
uspto-grants-2009_04
Patent number
USRE040703E1

Reaction notes

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