Water → Tert-butyl(pyridin-2-yloxy)acetate

HRID 1022731Notes

Reaction equation

HRID 1022731 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[OH:7].Br[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[C:13]([O:12][C:10](=[O:11])[CH2:9][O:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 178516071HCID 178516071, compound

Product 1

HCID 46168743Tert-butyl(pyridin-2-yloxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of pyridin-2-ol (1 g), tert-butyl bromoacetate (2.33 mL) and cesium carbonate (6.85 g) in DMF (20 mL) was stirred at 60° C. overnight. The reaction mixture was poured into water, and the mixture was partitioned twice with ethyl acetate. The organic layers were combined, and the mixture was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.18 g).

Workup

  1. customthe mixture was partitioned twice with ethyl acetate
  2. washthe mixture was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ee8e2ed4086f472f8b3ab8bcd82371bb
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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