Potassium Hydroxide → HCID 71236792, compound

HRID 920308Notes

Reaction equation

HRID 920308 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[O:5][C:6]1[N:11]=[CH:10][C:9]([CH:12](C(OCC)=O)[C:13]([O:15]CC)=[O:14])=[CH:8][CH:7]=1.[OH-].[K+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[O:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 71236577HCID 71236577, compound

Product 1

HCID 71236792HCID 71236792, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of diethyl 2-(6-(3,4-difluorophenoxy)pyridin-3-yl)malonate (25 g, 34.9 mmol) in ethanol (250 mL) was added potassium hydroxide (19.58 g, 349 mmol). The reaction mixture was stirred at 80° C. for 1 hr. and then the reaction mixture was concentrated under the reduced pressure. To the residue was added 10% HCl to adjust the solution to approximately pH 7. Then, the solution was extracted with EtOAc (300 mL), and the organic layer was separated, and dried over Na2SO4, and then concentrated under reduced pressure to give 2-(6-(3,4-difluorophenoxy)pyridin-3-yl)acetic acid (10 g, 98%).

Workup

  1. concentrationand then the reaction mixture was concentrated under the reduced pressure
  2. additionTo the residue was added 10% HCl
  3. extractionThen, the solution was extracted with EtOAc (300 mL)
  4. customthe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27ecf8a6168049b69ae6e8416dbf8aaf
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

Loading…