Water → 2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)4-methyl-6-(4,4,4-trifluorobut-1-enyloxy)pyridine

HRID 2229108Notes

Reaction equation

HRID 2229108 reaction equation
[I-].C[S+](C)(C)=O.[H-].[Na+].[CH3:9][N:10]1[C:14]([O:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([O:23][CH2:24]/[CH:25]=[CH:26]/[C:27]([F:30])([F:29])[F:28])[N:17]=2)=[CH:13][C:12]([C:31]([F:34])([F:33])[F:32])=[N:11]1.O>CS(C)=O>[CH3:9][N:10]1[C:14]([O:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([O:23][CH:24]=[CH:25][CH2:26][C:27]([F:30])([F:28])[F:29])[N:17]=2)=[CH:13][C:12]([C:31]([F:34])([F:32])[F:33])=[N:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 15477173(E)-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(4,4,4-trifluorobut-2-enyloxy)pyridine

Product 1

HCID 543102922-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)4-methyl-6-(4,4,4-trifluorobut-1-enyloxy)pyridineYield 3.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of trimethylsulfoxonium iodide (4.5 g, 20.5 mmol) in DMSO (50 ml) is added NaH (60% in oil, 0.82 g, 20.5 mmol) and the resulting mixture is stirred for 1 h at ambient temperature. To the resulting solution is added dropwise a solution of (E)-2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methyl-6-(4,4,4-trifluorobut-2-enyloxy)pyridine (example 1, 7.1 g, 18.6 mmol) at 10° C. After 3 h of stirring at ambient temperature, the dark mixture is hydrolyzed with water (200 ml) and extracted 3 times with diethylether (50 ml). The organic fractions are washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v) yields the title compound (0.22 g, 3.1% yield) of m.p. 56° C.

Workup

  1. stirringAfter 3 h of stirring at ambient temperature
  2. extractionextracted 3 times with diethylether (50 ml)
  3. washThe organic fractions are washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

Sources & evidence

ORD record
ord-87b64ca07389445f890bdd17a8fb9838
Source dataset
uspto-grants-2002_07
Patent number
US06420315B1

Reaction notes

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