Reaktion #64364

Reaktionsgleichung

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

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGby stirring at room temperature for 2 hours
3. 3
   workup.ADDITIONwas added
4. 4
   ExtraktionThe mixture was extracted with methylene chloride
5. 5
   Waschenthe organic layer was washed with water
6. 6
   Sonstigedried
7. 7
   SonstigeThe solvent was removed by distillation
8. 8
   Sonstigethe residue was purified by silica gel column chromatography (developing solution: CH2Cl2)

Vorschrift

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.

Quelle