Potassium trimethylsilanolate → 2-Fluoro-2-pyridin-2-ylpropanoic acid

HRID 1888161Notes

Reaction equation

HRID 1888161 reaction equation
[F:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:7])[C:3]([O:5]C)=[O:4].C[Si](C)(C)[O-].[K+]>C1COCC1>[F:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:7])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 66881466Methyl 2-fluoro-2-pyridin-2-ylpropanoate

Product 1

HCID 581251782-Fluoro-2-pyridin-2-ylpropanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.89 g (4.9 mmol) of methyl 2-fluoro-2-pyridin-2-ylpropanoate from Step A in 2 mL of anhydrous THF was added 1.3 g (9.7 mmol) of potassium trimethylsilanolate. The mixture was allowed to stir for 3 h at ambient temperature then quenched with 1 mL of trifluoroacetic acid. The volatiles were evaporated in vacuo and the resulting residue was purified by reverse phase HPLC (YMC Pack Pro C18, 100×20 mm I.D. column, 0-60% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient) to afford the title compound as a light yellow oil (785 mg, 95%). LC-MS: m/z (E/S) 170 (MH)+.

Workup

  1. customthen quenched with 1 mL of trifluoroacetic acid
  2. customThe volatiles were evaporated in vacuo
  3. customthe resulting residue was purified by reverse phase HPLC (YMC Pack Pro C18, 100×20 mm I.D. column, 0-60% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient)

Sources & evidence

ORD record
ord-ddcedaebfd7d492ca6c06468ba74755c
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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