Ethyl 4,4,4-trifluoroacetoacetate → HCID 178426304, compound

HRID 1289878Notes

Reaction equation

HRID 1289878 reaction equation
[CH3:1][C:2]1[C:3]([NH:8][NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[F:10][C:11]([F:21])([F:20])[C:12](=O)[CH2:13][C:14](OCC)=[O:15].C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:1][C:2]1[C:3]([N:8]2[C:14]([OH:15])=[CH:13][C:12]([C:11]([F:21])([F:20])[F:10])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 2508432-Hydrazinyl-3-methylpyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 178426304HCID 178426304, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-methyl-2-pyridylhydrazine (1.0 g, 8.13 mmol), acetic acid (7.0 mL) and ethyl trifluoroacetoacetate (1.2 mL, 8.13 mmol) was heated at 60° C. for 9 hours. The reaction mixture was neutralized with NaHCO3 and then was extracted with EtOAc (3×). The EtOAc extracts were combined, dried over MgSO4, filtered and concentrated to afford crude product which was purified by column chromatography on silica gel to afford 200 mg of 1-(3-methyl-2-pyridyl)-3-trifluoromethyl-5-hydroxypyrazole.

Workup

  1. extractionwas extracted with EtOAc (3×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-05265596895b4c30be818be8f12df043
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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