3-Fluoropentane-2,4-dione → 1-(2-Benzyloxyphenyl)-4-fluoro-3,5-dimethyl-1H-pyrazole

HRID 337353Notes

Reaction equation

HRID 337353 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][NH2:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:18][CH:19]([C:23](=O)[CH3:24])[C:20](=O)[CH3:21]>C(O)C>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]1[C:23]([CH3:24])=[C:19]([F:18])[C:20]([CH3:21])=[N:17]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 116266523-Fluoropentane-2,4-dioneHCID 12891836(2-(Benzyloxy)phenyl)hydrazine hydrochloride

Product 1

HCID 867032601-(2-Benzyloxyphenyl)-4-fluoro-3,5-dimethyl-1H-pyrazoleYield 70.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

500 mg of 2-benzyloxyphenyl hydrazine hydrochloride and 251 mg of 3-fluoropentane-2,4-dione were added to 12 ml of ethanol, and heated at reflux for 1.5 hours. The reaction solution was concentrated under reduced pressure as it is and purified using silica gel column chromatography (hexane:ethyl acetate=6:1 to 5:1) to yield 417 mg of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure as it
  4. custompurified

Sources & evidence

ORD record
ord-88a8dce911be426ba17e9c018908fdd3
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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