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

HRID 1007172Notes

Reaction equation

HRID 1007172 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-cd238d212d81494dbda0f998d1b0dd42
Source dataset
uspto-grants-2004_09
Patent number
US06794392B1

Reaction notes

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