Ethyl bromoacetate → Ethyl (4-methyl-1H-imidazol-1-yl)acetate

HRID 242255Notes

Reaction equation

HRID 242255 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.CC[O-].[Na+].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1)[CH3:17]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2723922Sodium ethoxideHCID 178418800HCID 178418800, compound

Product 1

HCID 237336Ethyl (4-methyl-1H-imidazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.4 g (53.6 mmol) 4-methyl-1H-imidazole are initially introduced into 20.0 ml (17.4 g, 53.6 mmol) 21% strength sodium ethylate solution in ethanol and 6.5 ml (9.8 g, 58.9 mmol) ethyl bromoacetate are added. The reaction mixture is stirred at RT for 16 h. For working up, the solid which has precipitated out is filtered off, the residue on the filter is washed with ethanol and the filtrate is concentrated in vacuo. The residue is purified by column chromatography over silica gel (mobile phase: acetonitrile/water 9:1). The product is obtained as a 3:2 mixture of the two regioisomers and is further reacted as such.

Workup

  1. additionare added
  2. customthe solid which has precipitated out
  3. filtrationis filtered off
  4. washthe residue on the filter is washed with ethanol
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe residue is purified by column chromatography over silica gel (mobile phase: acetonitrile/water 9:1)
  7. customThe product is obtained as a 3:2 mixture of the two regioisomers
  8. customis further reacted as such

Sources & evidence

ORD record
ord-cac646493da94a2c8be1d9b64133e524
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

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