Reaktion #65397

Reaktionsgleichung

sodium hydride

6-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine

cyclopentene oxide

→

6-cyano-3,4-dihydro-4-(2-hydroxycyclopentan-1-yl)-2,2-dimethyl-2H-1,4-benzoxazine

Lösungsmittel

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturafter cooling to room temperature
2. 2
   workup.STIRRINGThe mixture was stirred at 70° C. for 3 hours
3. 3
   Temperaturto cool
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe extract was washed with water and aqueous sodium chloride solution
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography
9. 9
   Sonstigethe resulting crude crystals were recrystallized from ethyl acetate-hexane

Vorschrift

In 20 ml of N,N-dimethylformamide was dissolved 1.0 g of 6-cyano-3,4-dihydro-2,2-dimethyl-2H-1,4-benzoxazine followed by addition of 0.24 g of sodium hydride. The mixture was stirred at 70° C. for 1 hour and after cooling to room temperature, 0.5 ml of cyclopentene oxide was added. The mixture was stirred at 70° C. for 3 hours. The reaction mixture was then allowed to cool, diluted with water and extracted with ethyl acetate. The extract was washed with water and aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography and the resulting crude crystals were recrystallized from ethyl acetate-hexane to give 0.53 g of 6-cyano-3,4-dihydro-4-(2-hydroxycyclopentan-1-yl)-2,2-dimethyl-2H-1,4-benzoxazine.

Quelle