Water → HCID 71616179, compound

HRID 871048Notes

Reaction equation

HRID 871048 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][O:6][C:7]1[CH:11]=[CH:10][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])[N:8]=1)C.[Li+].[OH-].O.[CH2:31]1COCC1>CO>[Br:19][C:17]1[CH:16]=[CH:15][C:14]([O:20][CH2:21][CH:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[C:13]([CH:18]=1)[CH2:12][N:9]1[C:10]([CH3:31])=[CH:11][C:7]([O:6][CH2:5][C:4]([OH:3])=[O:27])=[N:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86688755HCID 86688755, compound

Product 1

HCID 71616179HCID 71616179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of {1-[5-bromo-2-(2-ethyl-butoxy)-benzyl]-1H-pyrazol-3-yloxy}-acetic acid ethyl ester, 4, (0.017 g, 0.038 mmol) in a mixture of THF (1 mL) and methanol (0.5 ml) was added a solution of LiOH (0.05 g in 1 ml H2O). The resulting mixture was heated at 100° C. in an Emrys microwave reactor for 15 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 were removed in vacuo. The crude product was purified on silica to yield 0.016 g of {1-[5-bromo-2-(2-ethyl-butoxy)-benzyl]-5-methyl-1H-pyrazol-3-yloxy}-acetic acid, 5 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 were removed in vacuo
  5. customThe crude product was purified on silica

Sources & evidence

ORD record
ord-4a7141e385634d8c86d5a1543a4233ad
Source dataset
uspto-grants-2015_03
Patent number
US08969589B2

Reaction notes

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