Lithium hydroxide, monohydrate → 2-Ethoxy-3-[3-(3-{4-methanesulfonyloxyphenyl}propoxy)phenyl]propanoic acid

HRID 987238Notes

Reaction equation

HRID 987238 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:34])[CH:8]([O:31][CH2:32][CH3:33])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:22][CH:21]=2)[CH:11]=1)C>O.O1CCCC1>[CH2:32]([O:31][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][S:27]([CH3:30])(=[O:28])=[O:29])=[CH:24][CH:25]=2)[CH:11]=1)[C:7]([OH:34])=[O:6])[CH3:33]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22988419Ethyl 2-ethoxy-3-{3-[3-(4-methylsulfonyloxyphenyl)propoxy]phenyl}propanoate

Product 1

HCID 229887272-Ethoxy-3-[3-(3-{4-methanesulfonyloxyphenyl}propoxy)phenyl]propanoic acidYield 109.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium hydroxide hydrate (91.1 mg; 2.7 mmole) in water (6.6 ml) was slowly added to a solution of 2-ethoxy-3-{3-[3-(4-methanesulfonyloxyphenyl)propoxy]phenyl}propanoic acid ethyl ester (described in Example 12d) (0.889 g; 1.97 mmole) in tetrahydrofuran (9 ml). After stirring at room temperature for 5 hours tetrahydrofuran was removed by evaporation in vacuo. The residue was washed with diethyl ether and ethyl acetate. The water phase was acidified with potassium hydrogen sulfate (1M), and extracted with ethyl acetate and dichloromethane. The organic phases were combined, dried (sodium sulfate), filtered and the solvent was evaporated in vacuo to give 0.91 g of 2-ethoxy-3-[3-(3-{4-methanesulfonyloxyphenyl}propoxy)phenyl]propanoic acid.

Workup

  1. customwas removed by evaporation in vacuo
  2. washThe residue was washed with diethyl ether and ethyl acetate
  3. extractionextracted with ethyl acetate and dichloromethane
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-a940f089e2d942d4aee45e6d96ccafd5
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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