Hydrochloric Acid → HCID 58319261, compound

HRID 2363206Notes

Reaction equation

HRID 2363206 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([O:15]CC)=[O:14])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:19])[F:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67111220HCID 67111220, compound

Product 1

HCID 58319261HCID 58319261, compoundYield 73.8%

Reagents, catalysts & solvents 1

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

Procedure

Ethyl 5-[4-fluoro-3-(trifluoromethyl)phenyl]furan-2-carboxylate (136 mg, 0.45 mmol.) and LiOH (25 mg, 0.59 mmol) were diluted with THF/H2O=1:1 (3 mL), and then stirred for 1 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 (91 mg, 73%).

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-015704941c0b412f939bb0f9b1c8144e
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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