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Dimethylformamide → 4,4-difluoro-3-methyl-3-butenyl 3-methyl-1-phenyl-1H-pyrazole-4-carboxylate

HRID 917383
Notes
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Reaction equation

HRID 917383 reaction equation
CN(C)C=O.[CH3:6][C:7]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]=1.CS(O[CH2:26][CH2:27][C:28]([CH3:32])=[C:29]([F:31])[F:30])(=O)=O.C(=O)([O-])O.[Na+]>O>[CH3:6][C:7]1[C:11]([C:12]([O:14][CH2:26][CH2:27][C:28]([CH3:32])=[C:29]([F:31])[F:30])=[O:13])=[CH:10][N:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 52300563-methyl-1-phenyl-1H-pyrazole-4-carboxylic acidHCID 230202374,4-Difluoro-3-Methyl-3-Buten-1-Yl Methanesulfonate

Product 1

HCID 230203284,4-difluoro-3-methyl-3-butenyl 3-methyl-1-phenyl-1H-pyrazole-4-carboxylateYield 77%

Reagents, catalysts & solvents

1
HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 5 ml of N,N-dimethylformamide were dissolved 0.57 g (2.8 mmol) of 3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid, obtained in accordance with a method described in J. Chem. Soc., page 2736 (1961), and 0.58 g (2.9 mmol) of 4,4-difluoro-3-methyl-3-butenyl methanesulfonate, followed by the addition of 0.48 g (5.7 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:6) to obtain 0.66 g (yield: 76%) of 4,4-difluoro-3-methyl-3-butenyl 3-methyl-1-phenyl-1H-pyrazole-4-carboxylate.

Workup

  1. customobtained in accordance with a method
  2. customThe reaction liquid
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water
  5. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:6)

Sources & evidence

ORD record
ord-89e2f736f5c046fd98870d54cfb170f4
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07273878B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes