Hydrochloric Acid → 2-{4-[1-[4-(1H-pyrrol-1-yl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethanol

HRID 351261Notes

Reaction equation

HRID 351261 reaction equation
[OH-].[Na+].C([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH:30]=[CH:29][CH:28]=[CH:27]4)=[CH:22][CH:21]=3)[N:18]=[C:17]([C:31]([F:34])([F:33])[F:32])[CH:16]=2)=[CH:11][CH:10]=1)(=O)C.Cl>C1COCC1.CO>[N:26]1([C:23]2[CH:24]=[CH:25][C:20]([N:19]3[C:15]([C:12]4[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][OH:6])=[CH:10][CH:11]=4)=[CH:16][C:17]([C:31]([F:33])([F:32])[F:34])=[N:18]3)=[CH:21][CH:22]=2)[CH:30]=[CH:29][CH:28]=[CH:27]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 210907052-{4-[1-[4-(1H-pyrrol-1-yl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate

Product 1

HCID 210907042-{4-[1-[4-(1H-pyrrol-1-yl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethanolYield 83.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1M NaOH (436 μl) was added to a solution of 2-{4-[1-[4-(1H-pyrrol-1-yl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethyl acetate (128 mg) in THF (1.5 ml) and MeOH (0.3 ml) under ice bath cooling. The mixture was stirred at 0° C.˜ambient temperature for 2 hours. The mixture was neutralized with 1M HCl (436 μl), and was partitioned between AcOEt and H2O. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer silica gel chromatography developed by AcOEt/n-hexane=50%. The separated silica gel was extracted with 10% MeOH/CHCl3 and the solvent was evaporated in vacuo to give 2-{4-[1-[4-(1H-pyrrol-1-yl)phenyl]-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenyl}ethanol (96.5 mg) as an amorphous powder.

Workup

  1. temperaturecooling
  2. customwas partitioned between AcOEt and H2O
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin layer silica gel chromatography
  7. extractionThe separated silica gel was extracted with 10% MeOH/CHCl3
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1ac06232fcfc42cf8a15d7aeb42a989f
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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