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

HRID 1982999Notes

Reaction equation

HRID 1982999 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.[CH2:10]=[O:11].C(N(CC)CC)C>CC(C)=O>[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][N:5]([CH2:10][OH:11])[N:4]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8471TriethylamineHCID 18070343-(Trifluoromethyl)pyrazole

Product 1

HCID 23149202[3-(trifluoromethyl)-1H-pyrazol-1-yl]methanolYield 86.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 4.08 g of 3-(trifluoromethyl)-1H-pyrazole, 2.00 g of paraformaldehyde and 1 ml of triethylamine was stirred at 80° C. for 5 hours. After the reaction mixture was cooled to room temperature, acetone was added to the reaction mixture. The mixture was filtered. The filterate was concentrated under reduced pressure. Hexane was added to the residue, and then crystalline was formed. The crystalline was collected to obtain 4.31 g of 3-(trifluoromethyl)-1H-pyrazole-1-ylmethanol.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationThe mixture was filtered
  3. concentrationThe filterate was concentrated under reduced pressure
  4. additionHexane was added to the residue
  5. customcrystalline was formed
  6. customThe crystalline was collected

Sources & evidence

ORD record
ord-1dc556a7a7964805b58ede2195bf92a1
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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