Water → {1-[5-Bromo-2-(2-ethyl-butoxy)-benzyl]-5-methyl-1H-pyrazol-4-yl}-acetic acid

HRID 575933Notes

Reaction equation

HRID 575933 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][C:6]1[CH:7]=[N:8][N:9]([CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C:10]=1[CH3:11])C.[Li+].[OH-].O>C1COCC1.CO>[Br:19][C:17]1[CH:16]=[CH:15][C:14]([O:20][CH2:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[C:13]([CH:18]=1)[CH2:12][N:9]1[C:10]([CH3:11])=[C:6]([CH2:5][C:4]([OH:27])=[O:3])[CH:7]=[N:8]1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 86688760{1-[5-bromo-2-(2-ethyl-butoxy)-benzyl]-5-methyl-1H-pyrazol-4-yl}-acetic acid ethyl ester

Product 1

HCID 71610574{1-[5-Bromo-2-(2-ethyl-butoxy)-benzyl]-5-methyl-1H-pyrazol-4-yl}-acetic acidYield 10%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of {1-[5-bromo-2-(2-ethyl-butoxy)-benzyl]-5-methyl-1H-pyrazol-4-yl}-acetic acid ethyl ester, 3, 0.1 g (0.22 mmol) in a mixture of THF (1 mL) and methanol (0.5 ml) was added a solution of LiOH (0.12 g in 1 ml H2O). The resulting mixture was heated at 100° C. on microwave for 20 minutes. The mixture was poured into water (20 mL) and extracted with EtOAc (3×15 mL). The organic layers were combined, washed with brine (30 mL), dried (MgSO4) and the volatiles removed in vacuo. The crude product was purified on silica to yield 7.4 mg (10%) of {1-[5-Bromo-2-(2-ethyl-butoxy)-benzyl]-5-methyl-1H-pyrazol-4-yl}-acetic acid, 4 as a white solid.

Workup

  1. extractionextracted with EtOAc (3×15 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customthe volatiles removed in vacuo
  5. customThe crude product was purified on silica

Sources & evidence

ORD record
ord-b82b32b8355648ce9cb77864dd32d23c
Source dataset
uspto-grants-2015_05
Patent number
US09035071B2

Reaction notes

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