Methyl iodide → HCID 86746472, compound
Reaction equation
[CH:1]([N-]C(C)C)(C)[CH3:2].[Li+].[C:9]([O-:14])(=[O:13])[CH2:10][CH:11]=C.[CH2:15]([C:19]1[N:20]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[Cl:43])[C:21](/[CH:24]=[C:25](\[CH2:30][C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)/C(OC)=O)=[CH:22][N:23]=1)[CH2:16][CH2:17][CH3:18].CI>O1CCCC1.[Cl-].[NH4+]>[CH2:15]([C:19]1[N:20]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[Cl:43])[C:21](/[CH:24]=[C:25](\[CH2:30][C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)/[CH:10]([CH3:11])[C:9]([O:14][CH2:1][CH3:2])=[O:13])=[CH:22][N:23]=1)[CH2:16][CH2:17][CH3:18]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Lithium diisopropylamide (0.85 mmol, 1M in tetrahydrofuran) is cooled to -78° under argon and a solution of ethyl (E)-4-[2-n-butyl-1-{(2-chlorophenyl)methyl)-1H-imidazol-5-yl]-3-(2-thienyl)methyl)-3-butenoate (0.709 mmol), prepared as in Example 13 using methyl (E) 3-[2-n-butyl-1-[(2-chlorophenyl)methyl]-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate (Example 1), in tetrahydrofuran (5 mL) is added. After 10 minutes methyl iodide (0.71 mmol) is added. The mixture is then stirred at room temperature overnight, diluted with 10% ammonium chloride and extracted with ethyl acetate. The dried, concentrated product is chromatographed over silica gel with 6:4 hexane/ethyl acetate to give the title compound.
Workup
- extractionextracted with ethyl acetate
- customThe dried, concentrated product is chromatographed over silica gel with 6:4 hexane/ethyl acetate
Sources & evidence
- ORD record
- ord-cb528caf3d54485da4aa791594d45e7a
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05185351
Reaction notes
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