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

HRID 1019039Notes

Reaction equation

HRID 1019039 reaction equation
C([N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25]/[CH:26]=[CH:27]/[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)[CH:29]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C.Cl>CO>[NH:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25]/[CH:26]=[CH:27]/[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([C:38]2[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=2)[CH:29]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 18399515Methyl 4-[(E)-3-(1-tritylimidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate

Product 1

HCID 18399528methyl 4-[(E)-3-(imidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoateYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-[(E)-3-(1-tritylimidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate (5.78 g; 6.5 mmol), acetic acid (5 ml) and 12N HCl (5 ml) in methanol (100 ml) was refluxed for 1 hour 30 minutes. After evaporation to dryness, the residue was neutralised with aqueous NH4 OH, extracted with dichloromethane, evaporated and purified by flash chromatography, eluting with dichloromethane/ethanol (98/2) to give methyl 4-[(E)-3-(imidazol-2-yl)prop-1-en-1-yl]-2-(4-fluorophenyl)benzoate. Yield: 63%

Workup

  1. customAfter evaporation to dryness
  2. extractionextracted with dichloromethane
  3. customevaporated
  4. custompurified by flash chromatography
  5. washeluting with dichloromethane/ethanol (98/2)

Sources & evidence

ORD record
ord-21d71dd20e8e4cfcad6e049a4c0d3da4
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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