Chloromethyl Methyl Ether → 1-Methoxymethyl-1H-imidazole-4-carboxylic acid methylester

HRID 242380Notes

Reaction equation

HRID 242380 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][NH:8][CH:9]=1)=[O:4].Cl[CH2:11][O:12][CH3:13]>C(#N)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][N:8]([CH2:11][O:12][CH3:13])[CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 178418785HCID 178418785, compound

Product 1

HCID 866747291-Methoxymethyl-1H-imidazole-4-carboxylic acid methylester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Imidazole-4-carboxylic acid methylester (5.00 g) was dissolved in acetonitrile (100 mL), and under ice cooling and stirring, were added TEA (11.1 mL) and then chloromethylmethylether (4.47 mL), followed by heating to reflux for 3 days. After being allowed to cool to room temperature, the mixture was diluted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (methanol/chloroform=0%→7%) using silica gel column (product name: Hi-Flash Column 5 L, manufactured by Yamazen Corporation) to afford the title compound (3.64 g).

Workup

  1. temperatureby heating
  2. temperatureto reflux for 3 days
  3. washwashed with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by flash chromatography (methanol/chloroform=0%→7%)

Sources & evidence

ORD record
ord-e42ab8fdf2c6459e90fb6d0ea0ab256d
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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