Reaktion #46525

Reaktionsgleichung

Dimethyl sulfide

8-benzylidene-5,6,7,8-tetrahydro-quinoline

ozone

→

title compound

Ausbeute 79.0%

6,7-Dihydro-5H-quinolin-8-one

Ausbeute 79.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated in vacuo
2. 2
   Sonstigethe residue was purified by flash chromatography on silica gel (EtOAc)

Vorschrift

A solution of 8-benzylidene-5,6,7,8-tetrahydro-quinoline (4.30 g, 19.4 mmole) in CH2Cl2 (150 mL) was reacted with ozone at −78° C. for 30 minutes. Dimethyl sulfide (5 mL) was added, and the reaction was warmed to RT and stirred overnight. The mixture was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (EtOAc). The title compound (2.20 g, 79%) was obtained as an off-white solid after drying in vacuo: MS (ES) m/e 148 (M+H)+.

Quelle