Ethyl bromoacetate → Ethyl 3-(2-ethoxy-2-oxoethoxy)picolinate

HRID 1984286Notes

Reaction equation

HRID 1984286 reaction equation
[OH:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:10][C:8]([C:3]1[C:2]([O:1][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 15080989Ethyl 3-hydroxypicolinate

Product 1

HCID 21793317Ethyl 3-(2-ethoxy-2-oxoethoxy)picolinateYield 82.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 3-hydroxy-picolinate (11.0 g, 65.8 mmol), ethyl bromoacetate (12.1 g, 72.4 mmol) and anhydrous potassium carbonate (11.8 g, 85.5 mmol) in acetone (120 mL) was heated under reflux for 15 h. After cooling, the inorganic material separated by filtration. The filtrate was dissolved in chloroform, washed with water, then brine and dried (MgSO4), filtered, and the solvent was evaporated to give a brown oily residue. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give ethyl 2-(2-ethoxycarbonyl-3-pyridyloxy)acetate (13.7 g) as a yellow oil (13.7 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 h
  3. temperatureAfter cooling
  4. customthe inorganic material separated by filtration
  5. dissolutionThe filtrate was dissolved in chloroform
  6. washwashed with water
  7. dry with materialbrine and dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customto give a brown oily residue
  11. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-57c4a3b67f9b4d5b90b1641d493067d9
Source dataset
uspto-grants-2009_06
Patent number
US07544693B2

Reaction notes

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