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

HRID 1409391Notes

Reaction equation

HRID 1409391 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

HCID 86714651Methyl 2-(1-ethoxyvinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Product 1

HCID 70981298Methyl 2-acetyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

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).

Workup

  1. additionwas added at RT
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with DCM
  4. customThe organic layer was evaporated
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f06224c0005643049d6b18c808f7ac8c
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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