Hydrochloric Acid → HCID 9843492, compound

HRID 987326Notes

Reaction equation

HRID 987326 reaction equation
O.[OH-].[Li+].C([O:6][C:7](=[O:32])[CH:8]([O:29][CH2:30][CH3:31])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[CH:12][CH:11]=1)C.Cl>O.O1CCCC1>[CH2:30]([O:29][CH:8]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][CH:24]=2)=[CH:12][CH:11]=1)[C:7]([OH:32])=[O:6])[CH3:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrate2×HCID 54531001HCID 54531001, compound

Product 1

HCID 9843492HCID 9843492, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (57 mg; 1.37 mmole) dissolved in water (2 ml) was added to a solution of 2-ethoxy-3-{4-[2-(4-methanesulfonylphenyl)ethoxy]phenyl}propanoic acid ethyl ester (described in Example 87) (384 mg; 0.91 mmole) in tetrahydrofuran 6 ml. After stirring at room temperature for 2 hours more lithium hydroxide hydrate (30 mg) dissolved in water (1 ml) was added. The reaction mixture was stirred at room temperature for 4 more hours. The reaction mixture was acidified with hydrochloric acid (2 M) to pH 4. Tetrahydrofuran was evaporated in vacuo, water (5 ml) was added and the product was extracted with ethyl acetate (10 ml). The organic phase was washed with water, dried (sodium sulfate) and the solvent was evaporated in vacuo. Purification by chromatography on silica gel using heptane:ethyl acetate:acetic acid (10:10:1) as eluant gave 0.307 g (yield 86%) of 2-ethoxy-3-{4-[2-(4-methanesulfonylphenyl)ethoxy]phenyl}propanoic acid as a pale yellow oil that crystallizes when vacuum dried.

Workup

  1. additionwas added
  2. customTetrahydrofuran was evaporated in vacuo, water (5 ml)
  3. additionwas added
  4. extractionthe product was extracted with ethyl acetate (10 ml)
  5. washThe organic phase was washed with water
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent was evaporated in vacuo
  8. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-2c73c857a2124b37a4257acae2868204
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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