Methyl iodide → Methyl 3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate

HRID 265909Notes

Reaction equation

HRID 265909 reaction equation
[H-].[Na+].Cl.[NH:4]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12])[N:6]=[CH:5]1.[CH3:15]I>CCOC(C)=O.O>[CH3:15][N:4]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12])[N:6]=[CH:5]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178500033HCID 178500033, compound

Product 1

HCID 54549961Methyl 3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (0.85 g of a 60% dispersion in oil, 21.2 mmol) was placed in a flask, suspended in hexanes, and allowed to settle. The hexanes was decanted and DMF (50 mL) was added, followed by 35-2 (2 g, 10.6 mmol). After 10 minutes methyl iodide (0.79 mL, 12.7 mmol) was added. After stirring for 24 hr the solution was diluted with EtOAc and H2O and the layers were separated. The water layer was basified to pH 11 with saturated NaHCO3 and extracted with EtOAc and CH2Cl2. The organic layers were combined and evaporated. The residue was chromatographed (5% CH3OH/CHCl3 saturated with NH3) to give 35-3 as a white solid.

Workup

  1. customThe hexanes was decanted
  2. additionDMF (50 mL) was added
  3. customthe layers were separated
  4. extractionextracted with EtOAc and CH2Cl2
  5. customevaporated
  6. customThe residue was chromatographed (5% CH3OH/CHCl3 saturated with NH3)

Sources & evidence

ORD record
ord-584b3dce1e0642a6917e3e9fc77e36b1
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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