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

Participants

Reaction Steps

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)+.

Provenance & Evidence