반응 #64364

반응 방정식

diethyl-aluminum cyanide

NaOH

7,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole

→

8-cyano-6,6-dimethyl-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole

용매

toluene

toluene

반응 조건

후처리

1. 1
   온도cooling
2. 2
   workup.STIRRINGby stirring at room temperature for 2 hours
3. 3
   workup.ADDITIONwas added
4. 4
   추출The mixture was extracted with methylene chloride
5. 5
   세척the organic layer was washed with water
6. 6
   기타dried
7. 7
   기타The solvent was removed by distillation
8. 8
   기타the residue was purified by silica gel column chromatography (developing solution: CH2Cl2)

실험 절차

To a mixture of 3.9 g of 7,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole and 80 ml of toluene was added dropwise 90 ml of a 1.0M solution of diethyl-aluminum cyanide in toluene with stirring under ice-cooling, followed by stirring at room temperature for 2 hours. The reaction mixture was poured into ice-water, and 2N NaOH was added thereto. The mixture was extracted with methylene chloride, and the organic layer was washed with water and dried. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography (developing solution: CH2Cl2) to obtain 2.9 g of 8-cyano-6,6-dimethyl-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole represented by formula shown below.

출처