Reaktion #364094

Reaktionsgleichung

sodium hydride

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

1,4-dibromobutane

→

title compound

Ausbeute 43.3%

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

Ausbeute 43.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to −40° C
2. 2
   workup.STIRRINGthe mixture was stirred overnight
3. 3
   Temperaturwhile gradually increasing the temperature in an atmosphere of argon
4. 4
   ExtraktionThe reaction solution was extracted with ethyl acetate
5. 5
   Waschenwashed with water
6. 6
   TrocknenAfter drying (Na2SO4)
7. 7
   Sonstigethe oily substance obtained by the evaporation of the solvent under a reduced pressure
8. 8
   Sonstigewas purified by a silica gel column chromatography (700 cc; elution with ethyl acetate-hexane=2:3)
9. 9
   Sonstigerecrystallized from ethyl acetate-hexane

Vorschrift

A 170 ml portion of DMF solution of 6-acetyl-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (3.2 g, 14.9 mmol) was cooled to −5° C. Thereto was added 0.7 g of sodium hydride (16.4 mmol), and the resulting solution was stirred at 0° C. for 30 minutes and then cooled to −40° C. Thereto was added 8.9 ml of 1,4-dibromobutane (74.5 mmol), and the mixture was stirred overnight while gradually increasing the temperature in an atmosphere of argon. The reaction solution was extracted with ethyl acetate and washed with water. After drying (Na2SO4), the oily substance obtained by the evaporation of the solvent under a reduced pressure was purified by a silica gel column chromatography (700 cc; elution with ethyl acetate-hexane=2:3) and then recrystallized from ethyl acetate-hexane to obtain 2.26 g of the title compound (43% in yield).

Quelle