Hydrochloric Acid → HCID 960607, compound

HRID 2363204Notes

Reaction equation

HRID 2363204 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:13]2[O:17][C:16]([C:18]([O:20]CC)=[O:19])=[CH:15][CH:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Li+].[OH-].Cl>C1COCC1.O>[F:23][C:2]([F:1])([F:24])[C:3]1[CH:4]=[C:5]([C:13]2[O:17][C:16]([C:18]([OH:20])=[O:19])=[CH:15][CH:14]=2)[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86654784HCID 86654784, compound

Product 1

HCID 960607HCID 960607, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Ethyl 5-[3,5-bis(trifluoromethyl)phenyl]furan-2-carboxylate (61 mg, 0.17 mmol) and LiOH (9.4 mg, 0.22 mmol) were diluted with THF/H2O=1:1 (1.5 mL), and then stirred for 2 hrs at room temperature. The mixture was acidified with 1N HCl, concentrated under reduced pressure, and diluted with EtOAc and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to yield the crude title compound as a white solid (30 mg, 54%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85ec31a0201c477885b1e4b12b41cfd7
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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