Lithium Hydroxide → 4-(4'-Fluorobiphenyl-4-yl)-2-(methylsulfonyl)butanoic acid

HRID 533574Notes

Reaction equation

HRID 533574 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH:16]([S:22]([CH3:25])(=[O:24])=[O:23])[C:17]([O:19]CC)=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH:16]([S:22]([CH3:25])(=[O:24])=[O:23])[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 66577988Ethyl 4-(4'-fluorobiphenyl-4-yl)-2-(methylsulfonyl)butanoate

Product 1

HCID 665780134-(4'-Fluorobiphenyl-4-yl)-2-(methylsulfonyl)butanoic acidYield 87.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(4′-fluorobiphenyl-4-yl)-2-(methylsulfonyl)butanoate in THF (2.2 mL) and methanol (0.6 mL) was added a solution of lithium hydroxide in water (37 mg, 1.54 mmol, 0.6 mL water) and stirred at room temperature for 30 minutes. The mixture was diluted with water (30 mL) and washed with Et2O 50 mL. The organic layer was discarded. The aqueous layer was acidified with 0.5N HCl and the white suspension was re-extracted with Et2O. The ether extract was washed with brine 50 mL, dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a white solid (113 mg, 87.5%) MS (LC/MS) m/z 335.1 (M−1)

Workup

  1. washwashed with Et2O 50 mL
  2. extractionthe white suspension was re-extracted with Et2O
  3. extractionThe ether extract
  4. washwas washed with brine 50 mL
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c65b7e78b06c4386be388b1404ac471f
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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