Tetrahydrofuran → 1-[1-(3,4-dichloro-phenyl)-1H-imidazol-4-yl]-ethanol

HRID 433590Notes

Reaction equation

HRID 433590 reaction equation
C[Mg]I.[Cl:4][C:5]1[CH:6]=[C:7]([N:12]2[CH:16]=[C:15]([CH:17]=[O:18])[N:14]=[CH:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11].[CH2:19]1COCC1.[Cl-].[NH4+]>CCOCC>[Cl:4][C:5]1[CH:6]=[C:7]([N:12]2[CH:16]=[C:15]([CH:17]([OH:18])[CH3:19])[N:14]=[CH:13]2)[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 234451021-(3,4-dichloro-phenyl)-1H-imidazole-4-carbaldehydeHCID 178418373HCID 178418373, compound

Product 1

HCID 234449581-[1-(3,4-dichloro-phenyl)-1H-imidazol-4-yl]-ethanolYield 93%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of methylmagnesium iodide in ether (3 M, 13,7 ml, 41.1 mmol) and ether (40 ml), 1-(3,4-dichloro-phenyl)-1H-imidazole-4-carbaldehyde (2.58 g, 10.7 mmol) was added in portions. THF (50 ml) was then added slowly and stirring was continued for 1 h at reflux. After the addition of aqueous ammonium chloride (saturated, 30 ml), the mixture was extracted with AcOEt. The organic phase was dried (Na2SO4) and evaporated to give 1-[1-(3,4-dichloro-phenyl)-1H-imidazol-4-yl]-ethanol (2.56 g, 93%) as a light brown solid. MS: m/e=257.0 (M+H+).

Workup

  1. temperatureat reflux
  2. extractionthe mixture was extracted with AcOEt
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-6475364b210c4c2eb043982bb907ee26
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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