Methyl 2-(1-ethoxyvinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate → Methyl 2-acetyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:18]([O:20]CC)=[CH2:19])[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=1)=[O:4]>C1COCC1.Cl>[C:18]([C:7]1[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:16])([CH3:15])[CH3:17])[CH:9]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[N:6]=1)(=[O:20])[CH3:19]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Into a flask containing a solution of methyl-2-(1-ethoxyvinyl)-1-((2-(tri-methylsilyl)-ethoxy)methyl)-1H-imidazole-4-carboxylate (3.5 g, 10.7 mmol) in THF (25 ml), 2 N HCl (25 ml) was added at RT and stirred for 3 h. The reaction mixture was concentrated and extracted with DCM. The organic layer was evaporated and the residue was purified by flash chromatography. Yield 2.6 g. 1H-NMR (400 MHz; CDCl3): δ −0.016 (s, 9H), 0.94 (t, 2H), 2.73 (s, 3H), 3.58 (t, 2H), 3.94 (s, 3H), 5.76 (s, 2H), 7.93 (s, 1H).