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

HRID 23317

반응식

HRID 23317 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d2471746428b47baab9624f8b8dea539
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852673B2

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