Perchloric Acid → (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate

Participants

Reaction Steps

To a stirred solution of (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-hydroxyethyl pivalate (330 mg, 0.87 mmol) in t-butylacetate (10 mL) was added perchloric acid (0.3 mL, 3.5 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours, quenched with slow addition of NaHCO3 solution. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate. LCMS-ESI+ (m/z): [M+H]+ calc'd for C22H31BrNO3: 436.1; Found: 436.2.

Provenance & Evidence