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

HRID 523256Notes

Reaction equation

HRID 523256 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:9][C:10]([O:12]CC)=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1.[OH-].[Na+:16]>C1COCC1>[CH3:1][O:2][C:3]1[C:4]([CH2:9][C:10]([O-:12])=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1.[Na+:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59636754Ethyl 2-(3-methoxypyridin-2-yl)acetate

Product 1

HCID 117761184Sodium 2-(3-methoxypyridin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of ethyl 2-(3-methoxypyridin-2-yl)acetate (0.17 g, 0.871 mmol) in THF (2.5 mL) at room temperature was treated with 3 M aqueous NaOH (0.581 mL, 1.74 mmol). After 7 h, the mixture was concentrated to remove the THF and the aqueous residue was frozen on dry ice and lyophilized to provide sodium 2-(3-methoxypyridin-2-yl)acetate as a white solid. A quantitative yield was assumed and the material used without further purification. Mass spectrum m/z 168 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated
  2. customto remove the THF
  3. temperaturethe aqueous residue was frozen on dry ice

Sources & evidence

ORD record
ord-6033f8b9fcf94c9f8f2b5acde39a0a88
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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