Water → HCID 8027287, compound

HRID 1056658Notes

Reaction equation

HRID 1056658 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.[K+].[K+].O>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

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178516071HCID 178516071, compound

Product 1

HCID 8027287HCID 8027287, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of crude hydroxy-pyridine 22b (30.0 g, 0.151 mol), bromo-acetic acid ethyl ester (16.9 ml, 0.151 mol) and K2CO3 (41.7 g, 0.301 mol) in acetone (1000 mL) is heated to reflux for 5 h. The mixture is cooled to RT, poured into water (800 mL) and extracted with EtOAc (500 mL×2). The combined organic layers are washed with brine, dried (Na2SO4). The solvent is evaporated and the residue is purified by column to afford ester 22c.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 5 h
  3. extractionextracted with EtOAc (500 mL×2)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent is evaporated
  7. customthe residue is purified by column

Sources & evidence

ORD record
ord-27c9185e0a9e4a9080879b076d3d4458
Source dataset
uspto-grants-2016_07
Patent number
US09399645B2

Reaction notes

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