반응 #65397

반응 방정식

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

용매

N,N-dimethylformamide

water

반응 조건

후처리

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

실험 절차

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.

출처