Reaktion #364099

Reaktionsgleichung

1,2-dichloroethane

triphosgene

1,2-dichloroethane

aluminum chloride

2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

→

title compound

Ausbeute 35.0%

6-Methoxycarbonyl-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]-indole-2(1H)-one

Ausbeute 35.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at a room temperature for 1 hour
2. 2
   Extraktionextracted with chloroform
3. 3
   Waschenwashed with 1 N hydrochloric acid
4. 4
   TrocknenAfter drying (Na2SO4)
5. 5
   Sonstigethe solvent was evaporated under a reduced pressure
6. 6
   Sonstigethe thus obtained oily substance was purified by a silica gel column chromatography (300 cc; elution with ethyl acetate-hexane=1:1)
7. 7
   Sonstigerecrystallized from ethyl acetate-hexane

Vorschrift

A 1.44 g (4.87 mmol) portion of triphosgene was added to 1,2-dichloroethane suspension (30 ml) of aluminum chloride (1.95 g, 14.61 mmol) and the mixture was cooled to 0° C. Thereto was added 30 ml of 1,2-dichloroethane solution containing 1.50 g (1.64 mmol) of 2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one, subsequently carrying out 2 hours of stirring at 0° C. The reaction solution was mixed with 50 ml of methanol, stirred at a room temperature for 1 hour, extracted with chloroform and then washed with 1 N hydrochloric acid. After drying (Na2SO4), the solvent was evaporated under a reduced pressure, and the thus obtained oily substance was purified by a silica gel column chromatography (300 cc; elution with ethyl acetate-hexane=1:1) and then recrystallized from ethyl acetate-hexane to obtain 0.63 g of the title compound (35% in yield).

Quelle