Ethanol → 2-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenol

HRID 537562Notes

Reaction equation

HRID 537562 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[N:16]2)=[CH:11][C:10]=1[CH3:24])C1C=CC=CC=1.C(O)C.[H][H]>[OH-].[OH-].[Pd+2].C1COCC1>[CH3:24][C:10]1[CH:11]=[C:12]([N:15]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[N:16]2)[CH:13]=[CH:14][C:9]=1[OH:8]

Participants

6

Reactant 3

HCID 702EthanolHCID 681565621-(4-(benzyloxy)-3-methylphenyl)-4-(trifluoromethyl)-1H-pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 681562662-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenolYield 86.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-(benzyloxy)-3-methylphenyl)-4-(trifluoromethyl)-1H-pyrazole (670 mg, 2.0 mmol), 20% palladium hydroxide on activated carbon (50 mg), ethanol (20 ml), and THF (20 ml) was shaken under 40 psi of hydrogen gas at the ambient temperature for 3 days and at +50° for 1 day, to drive reaction to completion. The reaction was filtered through a pad of Celite and the mother liquor was concentrated to obtain the target product as a colorless solid (420 mg, 86%). MS (M+1): 243.0.

Workup

  1. customreaction to completion
  2. filtrationThe reaction was filtered through a pad of Celite
  3. concentrationthe mother liquor was concentrated

Sources & evidence

ORD record
ord-cee29c5d5b734b6d84651e2ac1fc04c5
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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