3-benzyloxy-4-(4-ethylbenzyl)-1-isopropyl-5-methyl-1H-pyrazole → HCID 178436197, compound

HRID 2116476Notes

Reaction equation

HRID 2116476 reaction equation
C([O:8][C:9]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=2)=[C:12]([CH3:23])[N:11]([CH:24]([CH3:26])[CH3:25])[N:10]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH2:21]([C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:13]2[C:9]([OH:8])=[N:10][N:11]([CH:24]([CH3:25])[CH3:26])[C:12]=2[CH3:23])=[CH:16][CH:17]=1)[CH3:22]

Participants

4

Reactant 1

HCID 231036073-benzyloxy-4-(4-ethylbenzyl)-1-isopropyl-5-methyl-1H-pyrazole

Product 1

HCID 178436197HCID 178436197, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of the thus obtained 3-benzyloxy-4-(4-ethylbenzyl)-1-isopropyl-5-methyl-1H-pyrazole (160 mg, 0.46 mmol) in methanol (3 mL), 20% palladium hydroxide/carbon (58 mg) was added at room temperature and stirred overnight under a hydrogen atmosphere at room temperature. After filtration to remove the insoluble materials, the solvent was distilled off under reduced pressure to give 4-(4-ethylbenzyl)-3-hydroxy-1-isopropyl-5-methyl-1H-pyrazole (109 mg, 92%) as a colorless powder.

Workup

  1. filtrationAfter filtration
  2. customto remove the insoluble materials
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-26cf68b0cf5244d08be43b39ea493a5f
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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