Reaktion #364098

Reaktionsgleichung

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

sodium methoxide

→

title compound

Ausbeute 56.0%

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

Ausbeute 56.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter neutralization of the reaction solution with an ion exchange resin Amberlite 15, the resin was removed by filtration
2. 2
   Sonstigethe solvent was evaporated under a reduced pressure
3. 3
   workup.DISSOLUTIONThe thus obtained oily substance was dissolved in 4 ml of acetone
4. 4
   workup.ADDITIONthe solution was mixed with 2 ml of methyl iodide and 2 ml of potassium carbonate aqueous solution
5. 5
   workup.STIRRINGstirred overnight at room temperature
6. 6
   ExtraktionThe reaction solution was extracted with ethyl acetate
7. 7
   Waschenwashed with 1 N hydrochloric acid
8. 8
   TrocknenAfter drying (Na2SO4)
9. 9
   Sonstigethe solvent was evaporated under a reduced pressure
10. 10
    Sonstigethe thus obtained oily substance was purified by a silica gel column chromatography (100 cc; elution with ethyl acetate-hexane=1:2)

Vorschrift

A 16 ml portion of methanol solution of 6-acetoxy-2a-(4-bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one (0.60 g, 1.64 mmol) was mixed with sodium methoxide and stirred at a room temperature for 3 hours. After neutralization of the reaction solution with an ion exchange resin Amberlite 15, the resin was removed by filtration and the solvent was evaporated under a reduced pressure. The thus obtained oily substance was dissolved in 4 ml of acetone, and the solution was mixed with 2 ml of methyl iodide and 2 ml of potassium carbonate aqueous solution and stirred overnight at room temperature. The reaction solution was extracted with ethyl acetate and 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 (100 cc; elution with ethyl acetate-hexane=1:2) to obtain 0.31 g of the title compound (56% in yield).

Quelle