Ethanol → HCID 86010495, compound

HRID 1750383Notes

Reaction equation

HRID 1750383 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH3:16]N(C(OC)OC)C.C(O)C.[C:27]1([NH:33][NH2:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:34]=[CH:16][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7516PhenylhydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 2758844Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Product 1

HCID 86010495HCID 86010495, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 3-(4-fluorophenyl)-3-oxopropanoate (1.50 g, 7.14 mmol) and DMFDMA (1.15 mL, 8.56 mmol) in toluene (23 mL) was heated under reflux for 15 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethanol (23 mL). To the ethanol solution was added phenylhydrazine (0.779 mL, 7.85 mmol) at room temperature, and the mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent; 2% ethyl acetate/hexane) to give ethyl 5-(4-fluorophenyl)-1-phenyl-1H-pyrazole-4-carboxylate (1.90 g, 86%) as a yellow powder.

Workup

  1. temperatureunder reflux for 15 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethanol (23 mL)
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 3 hr
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent; 2% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cd0d591210e148eaad144eb88e533be3
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

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