Sodium Hydroxide → Sodium 2-(3-fluoropyridin-2-yl)acetate

HRID 523266Notes

Reaction equation

HRID 523266 reaction equation
[F:1][C:2]1[C:3]([CH2:8][C:9]([O:11]CC)=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-].[Na+:15]>C1COCC1>[F:1][C:2]1[C:3]([CH2:8][C:9]([O-:11])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1.[Na+:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57447461Ethyl (3-fluoro-2-pyridyl)acetate

Product 1

HCID 117761161Sodium 2-(3-fluoropyridin-2-yl)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of ethyl 2-(3-fluoropyridin-2-yl)acetate (1.90 g, 10.4 mmol) in THF (26 mL) was treated with 3 M aqueous NaOH (6.9 mL, 20.7 mmol) and stirred at room temperature overnight. The mixture was concentrated to remove the THF, and the residual aqueous solution was frozen and lyophilized to provide sodium 2-(3-fluoropyridin-2-yl)acetate as a white solid (assumed 100% yield), which was used without further purification. Mass spectrum m/z 156 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the THF
  3. temperaturethe residual aqueous solution was frozen

Sources & evidence

ORD record
ord-ddb25d1aee764080adbfcc87fa58030f
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

Loading…