Sodium Hydroxide → 8-cyano-6,6-dimethyl-6H-pyrano[2,3-f]benzo-2,1,3-oxadiazole
Reaction equation
[CH3:1][C:2]1([CH3:16])[O:14][C:6]2=[CH:7][C:8]3[C:9]([CH:13]=[C:5]2[CH:4]2O[CH:3]12)=[N:10][O:11][N:12]=3.[C-:17]#[N:18].C([Al+]CC)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:17]([C:4]1[C:5]2[C:6](=[CH:7][C:8]3[C:9]([CH:13]=2)=[N:10][O:11][N:12]=3)[O:14][C:2]([CH3:16])([CH3:1])[CH:3]=1)#[N:18]Participants
5
Procedure
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.
Workup
- temperaturecooling
- stirringby stirring at room temperature for 2 hours
- additionwas added
- extractionThe mixture was extracted with methylene chloride
- washthe organic layer was washed with water
- customdried
- customThe solvent was removed by distillation
- customthe residue was purified by silica gel column chromatography (developing solution: CH2Cl2)
Sources & evidence
- ORD record
- ord-b502c6e4cc0a4d6583dbec6f921257dc
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05412117
Reaction notes
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