Lithium hydroxide, monohydrate → HCID 59610041, compound

HRID 1889167Notes

Reaction equation

HRID 1889167 reaction equation
C[O:2][C:3](=[O:29])[CH:4]([O:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.O.[OH-].[Li+]>C1COCC1.O>[F:28][C:22]1[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:21]=1[O:20][CH:4]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[C:3]([OH:29])=[O:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59610024HCID 59610024, compound

Product 1

HCID 59610041HCID 59610041, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2,4-difluoro-phenoxy)-[4-(tetrahydro-pyran-4-sulfonyl)-phenyl]-acetic acid methyl ester (0.35 g, 0.82 mmol) in THF (3 ml), was added lithium hydroxide monohydrate (0.035 g, 2.05 mmol) in 1 ml water and stirred overnight at room temperature. Solvent was removed under reduced pressure, residue obtained was taken into water (5 ml), extracted with diethyl ether (10 ml×2). Aqueous layer was acidified with 1 N HCl solution, and extracted with ethyl acetate (10 ml×3), washed with water and brine (20 ml, each) dried over anhydrous sodium sulfate, filtered and solvent was concentrated to provide (2,4-difluoro-phenoxy)-[4-(tetrahydro-pyran-4-sulfonyl)-phenyl]-acetic acid (0.28 gm).

Workup

  1. customSolvent was removed under reduced pressure, residue
  2. customobtained
  3. extractionextracted with diethyl ether (10 ml×2)
  4. extractionextracted with ethyl acetate (10 ml×3)
  5. washwashed with water and brine (20 ml
  6. dry with materialeach) dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationsolvent was concentrated

Sources & evidence

ORD record
ord-b333797ebd9d47ccafc219326ee53132
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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