Реакция #46525

Уравнение реакции

Dimethyl sulfide

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

ozone

→

title compound

Выход 79.0%

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

Выход 79.0%

Растворители

CH2Cl2

Условия реакции

Обработка

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

Методика

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)+.

Источник