Methanol → [3-(trifluoromethyl)-1H-pyrazol-5-yl]methanol

HRID 1162758Notes

Reaction equation

HRID 1162758 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:7]=[C:6]([C:8](Cl)=[O:9])[NH:5][N:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CO.CCOC(C)=O>C1COCC1>[F:12][C:2]([F:1])([F:11])[C:3]1[CH:7]=[C:6]([CH2:8][OH:9])[NH:5][N:4]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 178521110HCID 178521110, compound

Product 1

HCID 10877483[3-(trifluoromethyl)-1H-pyrazol-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(Trifluoromethyl)pyrazole-5-carbonyl chloride (500 mg, 2.52 mmol) was dissolved in THF (10 mL). The reaction mixture was put under a N2 atmosphere and LiAlH4 (191 mg, 5.03 mmol) was added portionwise. The reaction mixture was stirred at RT for 2 days before adding MeOH (10 mL). The reaction mixture was concentrated in vacuo to give a grey solid. EtOAc (20 mL) was added and the crude reaction product stirred at RT for 30 min. The resulting solid was filtered off and the filtrate concentrated in vacuo to give the crude product which was used without further purification in the next step.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a grey solid
  3. customthe crude reaction product
  4. stirringstirred at RT for 30 min
  5. filtrationThe resulting solid was filtered off
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-464708346f754ddbb737a84feee93315
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

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