Ethyl bromoacetate → HCID 8027287, compound

HRID 1056659Notes

Reaction equation

HRID 1056659 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=CN=1.[CH2:8]([O:10][C:11](=[O:14])[CH2:12]Br)C.C([O-])([O-])=O.[Na+].[Na+]>CC(C)=O>[CH3:8][O:10][C:11](=[O:14])[CH2:12][C@@H:2]1[CH2:7][CH2:6][CH2:5][O:1]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10340Sodium CarbonateHCID 178516071HCID 178516071, compound

Product 1

HCID 8027287HCID 8027287, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of hydroxypyridine 36e (152 g, 0.527 mol), ethylbromoacetate (141 g, 0.843 mol) and Na2CO3 (184.3 g, 1.738 mol) in acetone (2000 mL) is refluxed for 6 h. The aqueous phase is extracted with DCM. The combined organic extracts are washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (1-50% EtOAc in petroleum ether) yields ester 36f.

Workup

  1. extractionThe aqueous phase is extracted with DCM
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (1-50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-c7a4e5d7b13e43d2bf3b7cc822d2f10e
Source dataset
uspto-grants-2016_07
Patent number
US09399645B2

Reaction notes

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