Reaktion #2294216

Reaktionsgleichung

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

NaOH

→

desired product

(S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethanol

Lösungsmittel

THF

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe obtained residue was purified by flash chromatography

Vorschrift

To a stirred solution of (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate (50.0 g, 115 mmol) in THF (600 mL) and methanol (200 mL) was added 1M NaOH solution (300 mL, excess) at 0° C. The mixture was stirred at room temperature for 16 hours, diluted with water. 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 the desired product. LCMS-ESI+: calc'd for C17H22BrNO2: 352.1 (M+H+); Found: 352.1 (M+H+).

Quelle