Sodium borohydride → HCID 59831860, compound
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][C:12]#[N:13])[CH:8]=2)[CH:3]=[CH:2]1.[BH4-].[Na+]>CC(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][C:12]#[N:13])[CH:8]=2)[CH:3]=[CH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring suspension of 3-(1H-indol-6-yl)-3-phenyl-acrylonitrile XII (1.3 g, 5.3 mmol) in 2-propanol (30 ml), NaBH4 (1.3 g, 34 mmol) was added portionwise over 30 min. The mixture was heated at reflux for 110 hours while occasionally adding 2-propanol to maintain the original volume. The mixture was cooled to room temperature and concentrated. The residue was partitioned between Et2O and H2O. The organic layer was separated, washed with brine, dried over MgSO4, filtered and evaporated. The crude 3-(1H-indol-6-yl)-3-phenyl-propionitrile (1.2 g, 90% pure) was used without further purification for the next reaction.