Formaldehyde → 3-t-butyl-1H-pyrazole-1-ylmethanol

HRID 1982996Notes

Reaction equation

HRID 1982996 reaction equation
[C:1]([C:5]1[CH:9]=[CH:8][NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:10]=[O:11].C(N(CC)CC)C>CC(C)=O>[C:1]([C:5]1[CH:9]=[CH:8][N:7]([CH2:10][OH:11])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8471TriethylamineHCID 178441177HCID 178441177, compound

Product 1

HCID 231492083-t-butyl-1H-pyrazole-1-ylmethanolYield 67.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
130 °C

Procedure

The mixture of 1.28 g of 3-t-butyl-1H-pyrazole, 0.66 g of paraformaldehyde and 0.3 g of triethylamine was stirred at 130° C. for 7 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 1.07 g of 3-t-butyl-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-3ad356f316b54298948b54e8dff50236
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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