Imidazole → HCID 12922722, compound

HRID 476598Notes

Reaction equation

HRID 476598 reaction equation
[Na].[NH:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10]Br>CO>[CH3:7][O:8][CH:9]([O:12][CH3:13])[CH2:10][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 816722-Bromo-1,1-dimethoxyethaneHCID 5360545Sodium

Product 1

HCID 12922722HCID 12922722, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve sodium spheres (2.3 g) in dry methanol (100 ml) at room temperature, add imidazole (6.3 ml) and stir for 1 hour at room temperature. Add bromoacetaldehyde dimethylacetal (11.8 ml) and heat the resultant mixture overnight at reflux. Evaporate the solvent in vacuo, partition the resultant residue between EtOAc and water, dry the organic layer over MgSO4, and evaporate the solvent. Purify the resultant residue by flash chromatography on SiO2 (250 g), eluting with 4% CH3OH in CH2Cl2. Combine the desired fractions and evaporate the solvent to obtain (1-imidazolyl)acetaldehyde dimethylacetal.

Workup

  1. customat room temperature
  2. temperatureat reflux
  3. customEvaporate the solvent in vacuo
  4. custompartition the resultant residue between EtOAc and water
  5. dry with materialdry the organic layer over MgSO4
  6. customevaporate the solvent
  7. customPurify the resultant residue by flash chromatography on SiO2 (250 g)
  8. washeluting with 4% CH3OH in CH2Cl2
  9. customevaporate the solvent

Sources & evidence

ORD record
ord-cb797a99dbeb4af59fe9cceb87bd2f13
Source dataset
uspto-grants-1989_12
Patent number
US04885293

Reaction notes

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