反応 #46525

反応方程式

Dimethyl sulfide

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

ozone

→

title compound

収率 79.0%

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

収率 79.0%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   濃縮The mixture was concentrated in vacuo
2. 2
   その他the residue was purified by flash chromatography on silica gel (EtOAc)

実験手順

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)+.

出典