반응 #155349

반응 방정식

Triphenyl phosphine

carbon tetrachloride

THF

5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydro-quinoline 2-carboxy-(2-hydroxyethyl)amide

→

5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline 2-carboxy-(2-chloroethyl)amide

수율 58.0%

용매

water

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도under reflux for 2 hours
3. 3
   추출followed by extraction with dichloromethane
4. 4
   세척The thus-obtained organic layer was washed with water
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified
8. 8
   농축The purified material was concentrated to dryness under reduced pressure

실험 절차

Triphenyl phosphine (2.47 g, 9.8 mmol) and carbon tetrachloride (1.4 g, 9.1 mmol) were added to a THF solution (30 ml) of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydro-quinoline-2-carboxy-(2-hydroxyethyl)amide (3.0 g, 7.24 mmol) and heated under reflux for 2 hours. The mixture was cooled to room temperature, and water was then added thereto, followed by extraction with dichloromethane. The thus-obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:methanol=100:0→20:1). The purified material was concentrated to dryness under reduced pressure, giving a white powder of 5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-1,4-dihydroquinoline-2-carboxy-(2-chloroethyl)amide (1.8 g, yield: 58%).

출처