Methanol → HCID 67304384, compound

HRID 447173Notes

Reaction equation

HRID 447173 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13](O)=[O:14])[N:10]=[CH:9]2)=[CH:4][CH:3]=1.CO>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 173900481-(4-Fluorophenyl)-1H-imidazole-4-carboxylic acid

Product 1

HCID 67304384HCID 67304384, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(4-Fluoro-phenyl)-1H-imidazole-4-carboxylic acid is dissolved in THF. Borane tetrahydrofuran complex in THF is added dropwise. The reaction is refluxed for 2 h and stirred at room temperature overnight. The reaction mixture is then cooled to 0° C. and methanol is added dropwise. The solvents are evaporated and the residue is taken up in HCl and refluxed for 2 h. The reaction mixture is then cooled to 0° C. and sodium hydroxide solution is added dropwise. The desired compound [1-(4-fluoro-phenyl)-1H-imidazol-4-yl]-methanol is obtained.

Workup

  1. temperatureThe reaction is refluxed for 2 h
  2. temperatureThe reaction mixture is then cooled to 0° C.
  3. customThe solvents are evaporated
  4. temperaturerefluxed for 2 h
  5. temperatureThe reaction mixture is then cooled to 0° C.
  6. additionsodium hydroxide solution is added dropwise

Sources & evidence

ORD record
ord-d0035ed09e9045f59fca3eb97361ce8b
Source dataset
uspto-grants-2013_07
Patent number
US08481548B2

Reaction notes

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