Lithium Hydroxide → 4-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acid

HRID 1039224Notes

Reaction equation

HRID 1039224 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:22])[CH2:6][CH2:7][CH2:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[O:11][N:10]=1>O.O1CCOCC1>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12]1[O:11][N:10]=[C:9]([CH2:8][CH2:7][CH2:6][C:5]([OH:22])=[O:4])[CH:13]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 591677844-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acid methyl ester

Product 1

HCID 684928304-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acidYield 100.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Add a solution of LiOH (0.98 g, 40.86 mmol) in water (30 mL) to a rapidly stirred solution of 4-[5-(2-Methoxy-phenyl)-isoxazol-3-yl]-butyric acid methyl ester (2.25 g, 8.17 mmol) in dioxane (60 mL), stir at room temperature overnight Quench with 1N HCl solution and concentrate to remove the majority of the dioxane. Add 1N NaOH to adjust pH to 4-5, extract with EtOAc (×2). Dry combined organic layers over MgSO4 and concentrate to get 2.15 g yellow oil. Recrystallize from EtOAc/hexanes to afford the title compound (1.67 g, 78%). MS (IS) 262 (M+1)+.

Workup

  1. customQuench with 1N HCl solution
  2. concentrationconcentrate
  3. customto remove the majority of the dioxane
  4. additionAdd 1N NaOH
  5. extractionextract with EtOAc (×2)
  6. customDry
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-32d8e5aa0165464495406a8cc42e4357
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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