Reacción #46525

Ecuación de reacción

Dimethyl sulfide

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

ozone

→

title compound

Rendimiento 79.0%

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

Rendimiento 79.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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)+.

Fuente