Lithium Hydroxide → HCID 54289059, compound

HRID 2265951Notes

Reaction equation

HRID 2265951 reaction equation
C([O:3][C:4](=[O:14])[CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([Cl:13])=[CH:11][CH:12]=1)C.[Li+].[OH-]>C1COCC1.O>[Cl:13][C:10]1[N:9]=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:14])=[O:3])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86625522HCID 86625522, compound

Product 1

HCID 54289059HCID 54289059, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(6-Chloro-pyridin-3-yloxy)-acetic acid ethyl ester (800 mg, 3.71 mmol) in THF was added to a solution of 0.5 N-LiOH (2 eq) and the mixture was stirred for 1.5 hrs at room temperature. The resulting residue was dissolved in H2O, then washed three times with Et2O, and neutralized with 1N HCl to pH 5˜7. The solution was extracted three times with methylene chloride and then dried over anhyd. Na2SO4 and concentrated in vacuo to give (6-chloro-pyridin-3-yloxy)-acetic acid (300 mg, 36%).

Workup

  1. washwashed three times with Et2O
  2. extractionThe solution was extracted three times with methylene chloride
  3. customdried over anhyd
  4. concentrationNa2SO4 and concentrated in vacuo

Sources & evidence

ORD record
ord-a5de05c46bc74ca1b874ec719c180095
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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