Lithium Hydroxide → (2S)-2-Ethoxy-3-{4-[4-(4-nitrophenyl)butoxy]phenyl}propanoic acid

HRID 1375718Notes

Reaction equation

HRID 1375718 reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)=[CH:13][CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Li+]>C1COCC1.O>[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([N+:28]([O-:30])=[O:29])=[CH:26][CH:27]=2)=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86613338Ethyl (2S)-2-ethoxy-3-{4-[4-(4-nitrophenyl)butoxy]phenyl}propanoate

Product 1

HCID 69426350(2S)-2-Ethoxy-3-{4-[4-(4-nitrophenyl)butoxy]phenyl}propanoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (2S)-2-ethoxy-3-{4-[4-(4-nitrophenyl)butoxy]phenyl}propanoate (1.05 g, 2.527 mmol) was dissolved in THF (20 ml). Under stirring, lithium hydroxide (78.7 mg, 3.285 mmol) in water (10 ml) was added in. The mixture was stirred at room temperature overnight. It was evaporated in vacuum to remove THF. The residue was extracted with diethyl ether. The obtained water phase was acidified with 10% hydrochloric acid, pH -3 and then extracted with ethyl acetate (×2). The organic phases were combined and washed with water and brine and dried with magnesium sulfate. The solvent was evaporated in vacuum. The desired product (926 mg) was obtained, yield 95%.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customIt was evaporated in vacuum
  3. customto remove THF
  4. extractionThe residue was extracted with diethyl ether
  5. extractionextracted with ethyl acetate (×2)
  6. washwashed with water and brine
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent was evaporated in vacuum

Sources & evidence

ORD record
ord-6e7c29b4e5b14c139b3a2fe684c3879f
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

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