Sodium Hydroxide → 5-[3-(Imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoic acid

HRID 1019033Notes

Reaction equation

HRID 1019033 reaction equation
[OH-].[Na+].[N:3]1([CH2:8][CH:9]=[CH:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[C:15]([CH:20]=2)[C:16]([O:18]C)=[O:17])[CH:7]=[CH:6][N:5]=[CH:4]1>O.CO>[N:3]1([CH2:8][CH:9]=[CH:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[C:15]([CH:20]=2)[C:16]([OH:18])=[O:17])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53807049Methyl 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate

Product 1

HCID 545106535-[3-(Imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (0.8 g, 20 mmol) in distilled water (3 ml) was added to a solution of methyl 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate (E and Z isomers) (2.4 g;.6.6 mmol) in methanol (30 ml). The mixture was refluxed for 6 hours. After evaporation and acidification with 12N HCl to pH 6, the residue was extracted with dichloromethane and evaporated to dryness to give 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoic acid (mixture of E and Z isomers).

Workup

  1. temperatureThe mixture was refluxed for 6 hours
  2. customAfter evaporation and acidification with 12N HCl to pH 6
  3. extractionthe residue was extracted with dichloromethane
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-bb3020b532074303ab70a80eec906546
Source dataset
uspto-grants-2002_11
Patent number
US06486156B1

Reaction notes

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