반응 #591199

반응 방정식

1-(4-Chloromethylbenzyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one

thiophenol

→

5-(1,3-dioxolan-2-yl)-1-(4-phenylsulfanylbenzyl)-3,4-dihydro-1H-quinolin-2-one

수율 97.0%

용매

THF

반응 조건

후처리

1. 1
   온도by heating
2. 2
   온도under reflux for 7 hours
3. 3
   농축the reaction mixture was concentrated under reduced pressure
4. 4
   기타The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)
5. 5
   농축The purified product was concentrated to dryness under reduced pressure

실험 절차

1-(4-Chloromethylbenzyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (1.0 g, 2.79 mmol), thiophenol (0.37 ml, 3.63 mmol) and 1,8-diazabicyclo[5.4.0]undecene-7 (DBU) (0.84 ml, 5.59 mmol) were added to THF (30 ml), followed by heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 1.13 g (yield: 94%) of 5-(1,3-dioxolan-2-yl)-1-(4-phenylsulfanylbenzyl)-3,4-dihydro-1H-quinolin-2-one as a white solid.

출처