Potassium Carbonate → Methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 1409423Notes

Reaction equation

HRID 1409423 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=[CH:2]1.C([O-])([O-])=O.[K+].[K+].[CH3:16][Si:17]([CH2:20][CH2:21][O:22][CH2:23]Cl)([CH3:19])[CH3:18]>CN(C=O)C>[CH3:16][Si:17]([CH3:19])([CH3:18])[CH2:20][CH2:21][O:22][CH2:23][N:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178418785HCID 178418785, compound

Product 1

HCID 22954042Methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Into a flask containing methyl 1H-imidazole-4-carboxylate (5 g, 39.7 mmol) in DMF (70 ml), K2CO3 (13.7 g, 99.1 mmol), SEM-Cl (9.3 ml, 51.6 mmol) were added and stirred at 80° C. overnight. The reaction mixture was quenched by the addition of H2O and extracted with EtOAc. The organic layer was concentrated and purified by column chromatography. Yield 3.8 g. 1H-NMR (400 MHz; DMSO-d6): δ 0.05 (s, 9H), 0.80 (t, 2H), 3.47 (t, 2H), 3.74 (s, 3H), 5.30 (s, 2H), 7.91 (s, 1H), 8.01 (s, 1H). LC-MS: [M+1]=257.27.

Workup

  1. additionwere added
  2. customThe reaction mixture was quenched by the addition of H2O
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-eaeeab8f2cdb44ac812721b92c1ddcf4
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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