Lithium Hydroxide → 3-[3-tert-Butyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoic acid

HRID 353299Notes

Reaction equation

HRID 353299 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:25][CH:26]([O:32][CH2:33][CH3:34])[C:27]([O:29]CC)=[O:28])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([C:5]1[CH:6]=[C:7]([CH2:25][CH:26]([O:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][S:21]([CH3:24])(=[O:22])=[O:23])=[CH:16][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10300195Ethyl 3-[3-tert-butyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoate

Product 1

HCID 227084073-[3-tert-Butyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoic acidYield 81.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-[3-tert-butyl-4-(2-{4-[(methylsulfonyl)oxy]phenyl}ethoxy)phenyl]-2-ethoxypropanoate (0.025 g; 0.050 mmole) was dissolved in THF and water (2:1), 0.1 M lithium hydroxide (2 ml) was added and the reaction mixture was stirred over night. Water was added and the THF evaporated. The remaining water was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The organic phase was dried with magnesium sulfate. Evaporation gave 0.019 g (80% yield) of the product.

Workup

  1. customthe THF evaporated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. customEvaporation

Sources & evidence

ORD record
ord-9d148c8530e4490194e26169e591fb02
Source dataset
uspto-grants-2004_06
Patent number
US06750252B2

Reaction notes

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