Lithium hydroxide, monohydrate → HCID 22988678, compound

HRID 987249Notes

Reaction equation

HRID 987249 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:33])[CH:8]([O:30][CH2:31][CH3:32])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=2)[CH:11]=1)C>O.O1CCCC1>[CH2:31]([O:30][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:21][CH:20]=2)[CH:11]=1)[C:7]([OH:33])=[O:6])[CH3:32]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54411964HCID 54411964, compound

Product 1

HCID 22988678HCID 22988678, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium hydroxide hydrate (0.175 g; 4.18 mmole) in water (5 ml) was slowly added to a solution of 2-ethoxy-3-{3-[2-(4-methanesulfonyloxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester (described in Example 22) (1.66 g; 3.80 mmole) in tetrahydrofuran (17 ml) at 0° C. After stirring at room temperature for 2 hours tetrahydrofuran was removed by evaporation in vacuo. The residue was extracted with diethyl ether. The water phase was acidified with hydrochloric acid, and extracted with ethyl acetate. The organic phase was washed with brine, dried (sodium sulfate), filtered and the solvent was evaporated in vacuo to give 1.5 g (96.5% yield) of 2-ethoxy-3-{3-[2-(4-methanesulfonyloxyphenyl)ethoxy]-phenyl}propanoic acid.

Workup

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

Sources & evidence

ORD record
ord-56fe21622d864a319f9ed716feadca6f
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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