Reaktion #1018933

Reaktionsgleichung

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

mCPBA

→

desired product

Ausbeute 37.1%

(S)-5-bromo-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-2,7-dimethylquinoline 1-oxide

Ausbeute 37.1%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigebefore quenched with NaHCO3 solution
2. 2
   ExtraktionThe mixture was extracted with DCM (30 mL)
3. 3
   Waschenwashed with NaHCO3 solution, water and brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   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 (5E) (118 mg, 0.31 mmol) in chloroform (5 mL) was added mCPBA (209 mg, 77%, 0.93 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour before quenched with NaHCO3 solution. The mixture was extracted with DCM (30 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product (52 mg, 37%). LCMS-ESI+ (m/z): 452.1, 454.1 (M+H)+.

Quelle