Sodium Hydroxide → 5-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetic acid

HRID 1899077Notes

Reaction equation

HRID 1899077 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][C:14]([O:16]C)=[O:15])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH2:13][C:14]([OH:16])=[O:15])=[CH:10][C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11795515Methyl 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetate

Product 1

HCID 117947425-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetic acidYield 82.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetate (2 g) and 4N sodium hydroxide solution (3.7 ml) in tetrahydrofuran (20 ml) as stirred at ambient temperature for 1 hour. The mixture was diluted with water and washed with toluene. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was recrystallized from a mixture of ethanol and water to give pale orange crystals of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetic acid (1.6 g).

Workup

  1. washwashed with toluene
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-95ed160351b841f0b61cc6c42c9e8adb
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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