Sodium Cyanide → 9-Cyanomethyl-6,11-dihydro-11-oxodibenz[b,e]oxepin
Reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][O:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:8](=[O:17])[C:7]=2[CH:18]=1.[C-:19]#[N:20].[Na+]>CN(C)C=O.O>[C:19]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][O:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[C:8](=[O:17])[C:7]=2[CH:18]=1)#[N:20]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Dissolve 6.4 gm of the bromomethyl compound of Step C in 75 cc of dimethylformamide and add 2.95 gm of sodium cyanide. Stir the mixture at room temperature for 1.5 hours. Dilute with 600 cc of water and extract three times with ether. Wash the combined organics with water, dry and strip to a solid residue. Triturate in hexane and recover the solid by filtration.