Acetic Acid → methyl 4-[(E)-3-(imidazol-5-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate

HRID 1019044Notes

Reaction equation

HRID 1019044 reaction equation
C([N:20]1[C:24]([CH2:25]/[CH:26]=[CH:27]/[C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)[CH:29]=2)=[CH:23][N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.C(O)(=O)C>CO>[NH:20]1[C:24]([CH2:25]/[CH:26]=[CH:27]/[C:28]2[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([C:38]3[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=3)[CH:29]=2)=[CH:23][N:22]=[CH:21]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 18399521methyl 4-[(E)-3-(1-tritylimidazol-5-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate

Product 1

HCID 18399501methyl 4-[(E)-3-(imidazol-5-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoateYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[(E)-3-(1-tritylimidazol-5-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate (7.8 g; 10 mmol), 12N HCl (7.5 ml) and acetic acid (7.5 ml) in methanol (150 ml) was refluxed for 1 hour 30 minutes. After evaporation to dryness and neutralisation with an aqueous solution of ammonium hydroxide, the residue was extracted with dichloromethane and purified by flash chromatography, eluting with a gradient 2-5% ethanol/dichloromethane to give methyl 4-[(E)-3-(imidazol-5-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate. Yield: 20%.

Workup

  1. customAfter evaporation to dryness and neutralisation with an aqueous solution of ammonium hydroxide
  2. extractionthe residue was extracted with dichloromethane
  3. custompurified by flash chromatography
  4. washeluting with a gradient 2-5% ethanol/dichloromethane

Sources & evidence

ORD record
ord-4f9d94617da7487cb5dab8be5fedb884
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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