تفاعل #46525

معادلة التفاعل

Dimethyl sulfide

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

ozone

→

title compound

المردود 79.0%

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

المردود 79.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)+.

المصدر