Hydrochloric Acid → Cis-4-{6,6,6-Trifluoro-3-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-hex-1-enyl}-benzoic acid

HRID 1669308Notes

Reaction equation

HRID 1669308 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]\[CH:12]([C:19]2[CH:20]=[N:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C1COCC1>[F:18][C:15]([F:16])([F:17])[CH2:14][CH2:13][CH:12]([C:19]1[CH:20]=[N:21][C:22]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:30]=2)=[CH:23][CH:24]=1)/[CH:11]=[CH:10]\[C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:35])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86620360Cis-4-{6,6,6-Trifluoro-3-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-hex-1-enyl}-benzoic acid methyl ester

Product 1

HCID 86620359Cis-4-{6,6,6-Trifluoro-3-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-hex-1-enyl}-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cis-4-{6,6,6-Trifluoro-3-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-hex-1-enyl}-benzoic acid methyl ester (1.0 g, 2.0 mmol) is taken into THF (5.0 mL) and treated with NaOH (2.5 mL, 5.0 N), then refluxed under nitrogen. The reaction mixture is neutralized with HCl (2.5 mL, 5.0 N), extracted with ethyl ether, dried over sodium sulfate. Concentration gives the title compound.

Workup

  1. temperaturerefluxed under nitrogen
  2. extractionextracted with ethyl ether
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration

Sources & evidence

ORD record
ord-ea7569a34ecc48bdb672cfa41aa3e932
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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