Potassium Hydroxide → HCID 71236646, compound

HRID 920315Notes

Reaction equation

HRID 920315 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH:13](C(OCC)=O)[C:14]([O:16]CC)=[O:15])=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].[OH-].[K+]>C(O)C>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:26]([F:29])([F:27])[F:28]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 71236644HCID 71236644, compound

Product 1

HCID 71236646HCID 71236646, compoundYield 166.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of diethyl 2-(5-(4-chloro-3-(trifluoromethyl)phenoxy)pyridin-2-yl)malonate (6 g, 5.42 mmol) in ethanol (60 mL) was added potassium hydroxide (3.04 g, 54.2 mmol). The reaction mixture was stirred at 80° C. for 1 hr., and then concentrated under reduced pressure. The reaction mixture was adjusted to pH 7 with 10% aqueous HCl solution. The reaction mixture was extracted with 100 mL of EtOAc, and the organic layer was separated, dried over Na2SO4, and then concentrated under reduced pressure to provide 2-(5-(4-chloro-3-(trifluoromethyl)phenoxy)pyridin-2-yl)acetic acid (3 g, 100%).

Workup

  1. concentration, and then concentrated under reduced pressure
  2. extractionThe reaction mixture was extracted with 100 mL of EtOAc
  3. customthe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a783abe95c6f4b0d8036fc8f39b6c68c
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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