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

HRID 1616610Notes

Reaction equation

HRID 1616610 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-c0c63d8a9a804dd382299294d4177a7f
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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