반응 #346762

반응 방정식

aluminium chloride

6-Oxo-6-phenylhexanoyl chloride

ferrocene

Water

aluminium chloride

→

1-benzoyl-2-ferrocenylcyclopentene

수율 15.0%

용매

cyclohexane

methylene chloride

반응 조건

후처리

1. 1
   기타at room temperature
2. 2
   기타(90 min)
3. 3
   온도the reaction mixture was heated
4. 4
   온도under reflux for 90 minutes
5. 5
   추출the organic layer run off, and the aqueous layer extracted with methylene chloride (100 ml)
6. 6
   세척The combined organic layers were washed with water (3 × 200 ml)
7. 7
   건조dried (sodium sulphate)
8. 8
   기타to yield a brown oil

실험 절차

6-Oxo-6-phenylhexanoyl chloride (9.0g; 0.04 mole) and ferrocene (7.44g; 0.04 mole) in methylene chloride (150 ml) were stirred at 0° and aluminium chloride (5.34g; 0.04 mole) was added over 40 minutes at 0°. The mixture was stirred at 0° (2 hr), and then at room temperature (90 min). More aluminium chloride (4g; 0.03 mole) was added and the reaction mixture was heated under reflux for 90 minutes. Water was added, the organic layer run off, and the aqueous layer extracted with methylene chloride (100 ml). The combined organic layers were washed with water (3 × 200 ml), and dried (sodium sulphate) to yield a brown oil. The portion of this oil which was insoluble in hot cyclohexane was discarded and the remainder (2.7g) was subjected to preparative thin layer chromatography to yield 2.1g (15%) of pure 1-benzoyl-2-ferrocenylcyclopentene as a brown solid mp 136°-137°.

출처