تفاعل #65397

معادلة التفاعل

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

المذيبات

N,N-dimethylformamide

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر