반응 #65401

반응 방정식

3,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-2H-1,4-benzoxazine

sodium hydride

phenacyl bromide

→

3,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-4-phenacyl-2H-1,4-benzoxazine

수율 66.6%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 1 hour
2. 2
   workup.DISTILLATIONafter which the solvent was distilled off under reduced pressure
3. 3
   workup.ADDITIONThe residue was diluted with 50 ml of water
4. 4
   추출extracted with ethyl acetate
5. 5
   건조The extract was dried over anhydrous magnesium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was chromatographed on a silica gel column and elution
8. 8
   기타Recrystallization from ethyl acetate-ether

실험 절차

In an argon gas stream, 2.0 g of 3,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-2H-1,4-benzoxazine was added gradually to 0.4 g of 60% sodium hydride in oil in 40 ml of dry N,N-dimethylformamide. The mixture was stirred at room temperature for 1 hour and 2.68 g of phenacyl bromide was added. The mixture was stirred at room temperature for 1 hour, after which the solvent was distilled off under reduced pressure. The residue was diluted with 50 ml of water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was chromatographed on a silica gel column and elution was carried out with methylene chloride-ethyl acetate. Recrystallization from ethyl acetate-ether gave 2.04 g of 3,4-dihydro-2,2-dimethyl-6-nitro-3-oxo-4-phenacyl-2H-1,4-benzoxazine.

출처