4-[2,5-Dioxo-3-methyl-4-[(2-propenyloxy)methyl]-4-(3-trifluoromethylphenyl)imidazolidin-1-yl]-2-trifluoromethylbenzonitrile → 4-[2,5-Dioxo-4-hydroxymethyl-3-methyl-4-(3-trifluoromethylphenyl)imidazolidin-1-yl]-2-trifluoromethyl-benzonitrile
Reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:9]2([CH2:29][O:30]CC=C)[C:13](=[O:14])[N:12]([C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=3)[C:11](=[O:27])[N:10]2[CH3:28])[CH:6]=[CH:7][CH:8]=1>C(Cl)Cl>[O:27]=[C:11]1[N:10]([CH3:28])[C:9]([CH2:29][OH:30])([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:34])([F:35])[F:1])[CH:4]=2)[C:13](=[O:14])[N:12]1[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[C:17]([C:23]([F:26])([F:24])[F:25])[CH:16]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 782 mg of 4-[4-(3-Trifluoromethylphenyl)-2,5-dioxo-3-methyl-4-[(2-propenyloxy)methyl]imidazolidin-1-yl]-2-trifluoromethylbenzonitrile in DCM (5 mL), 662 μL of trifluoroborane-dimethylsulfide complex are added. The mixture is stirred 6 hours at room temperature, diluted with DCM, washed with an aqueous solution of sodium bicarbonate, dried over magnesium sulfate, concentrated and purified on silica gel (ethyl acetate/cyclohexane 0/100 to 50/50) to give the desired compound.