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

HRID 987244Notes

Reaction equation

HRID 987244 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:36])[CH:7]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=2)=[CH:11][CH:10]=1>O.O1CCCC1>[CH2:30]([O:29][CH:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:22][CH:23]=2)=[CH:11][CH:10]=1)[C:6]([OH:36])=[O:5])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 569752562-Hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl ester

Product 1

HCID 229886862-Hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acidYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (0.036 g; 0.85 mmole) dissolved in water (2.6 ml) was slowly added at room temperature to a solution of 2-hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid methyl ester (described in Example 16) (0.37 g; 0.77 mmole) in tetrahydrofuran (3.5 ml). The reaction mixture was stirred at room temperature for 3.5 hours and then evaporated to remove tetrahydrofuran. The residue was acidified with potassium hydrogen sulfate (1 M) until pH<2 and then extracted with ethyl acetate. The organic phase was washed with brine and dried. Evaporation to remove the solvent gave 0.349 g (97.5%) of 2-hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid.

Workup

  1. customevaporated
  2. customto remove tetrahydrofuran
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customdried
  6. customEvaporation
  7. customto remove the solvent

Sources & evidence

ORD record
ord-927f498c4fb14148ba8935b4c7765e73
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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