Reaktion #82785

Reaktionsgleichung

(4aR)-(10bR)-8-chloro-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

sodium hydroxide

ethyl iodide

→

desired product

(4aR)-(10bR)-8-chloro-4-ethyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux, about 66°, for about 16 hours
2. 2
   Sonstigethe layers were separated
3. 3
   SonstigeThe organic layer was evaporated to an oil, which
4. 4
   workup.DISSOLUTIONwas dissolved in ethyl acetate
5. 5
   Extraktionextracted three times with 100 mL portions of water
6. 6
   SonstigeIt was then dried
7. 7
   Sonstigeevaporated to half its volume while heptane
8. 8
   workup.ADDITIONwas added in portions
9. 9
   FiltrationThe resulting white crystalline product was filtered
10. 10
    Waschenwashed with heptane
11. 11
    Sonstigedried under vacuum at 25°

Vorschrift

A 9.4 g portion of (4aR)-(10bR)-8-chloro-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one was combined in a flask with 94 ml of THF, 20 mL of 50% aqueous sodium hydroxide and 9.36 g of ethyl iodide, and was stirred at reflux, about 66°, for about 16 hours. The mixture was cooled to ambient temperature, and the layers were separated. The organic layer was evaporated to an oil, which was dissolved in ethyl acetate and extracted three times with 100 mL portions of water. It was then dried and evaporated to half its volume while heptane was added in portions. The resulting white crystalline product was filtered, washed with heptane and dried under vacuum at 25° to obtain 3.15 g of the desired product, m.p. 108°-110°.

Quelle