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Methanol → 2-(4-Fluorophenethyl)-5-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]benzoic acid

HRID 1251910
Notes
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Reaction equation

HRID 1251910 reaction equation
[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:19][C:20]3[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=3)=[CH:13][C:9]=2[C:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].CO>O>[F:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH2:19][C:20]3[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=3)=[CH:13][C:9]=2[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 183243882-(4-Fluorophenethyl)-5-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]benzoate

Product 1

HCID 183243842-(4-Fluorophenethyl)-5-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]benzoic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of 2-(4-fluorophenethyl)-5-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]benzoate (1.5 g.), sodium hydroxide (0.62 g.), methanol (200 ml.) and water (30 ml.) was stirred at reflux for 16 hours. The mixture was then cooled, the methanol evaporated away and the residue diluted with water (100 ml.). It was then washed with dichloromethane and the aqueous phase separated, acidified with 1M aqueous citric acid (25 ml.) and extracted with dichloromethane. The extracts were dried and evaporated to dryness to give 2-(4-fluorophenethyl)-5-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]benzoic acid as a white foam (1.1 g).

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureThe mixture was then cooled
  3. customthe methanol evaporated away
  4. additionthe residue diluted with water (100 ml.)
  5. washIt was then washed with dichloromethane
  6. customthe aqueous phase separated
  7. extractionextracted with dichloromethane
  8. customThe extracts were dried
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-0c693c2a60c24fb5894068df55f0fe86
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06342765B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes