2,2,3,3-Tetrafluoro-1-propanol → 2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxy-6-(2,2,3,3-tetrafluoropropyloxy)pyridine

HRID 23321

Reaktionsgleichung

Reaktionsgleichung von HRID 23321
[F:1][C:2]([F:8])([CH:5]([F:7])[F:6])[CH2:3][OH:4].[H-].[Na+].[CH3:11][N:12]1[C:16]([O:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20](OC3N(C)N=C(C(F)(F)F)C=3)[N:19]=2)=[CH:15][C:14]([C:37]([F:40])([F:39])[F:38])=[N:13]1>S1(CCCC1)(=O)=O.CCCCC.C(OCC)(=O)C>[CH3:11][N:12]1[C:16]([O:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:4][CH2:3][C:2]([F:8])([F:1])[CH:5]([F:7])[F:6])[N:19]=2)=[CH:15][C:14]([C:37]([F:40])([F:39])[F:38])=[N:13]1

Komponenten

6

Edukt 3

HCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 24758Sodium hydrideHCID 225726302,6-Bis(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridine

Produkt 1

HCID 225726422-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxy-6-(2,2,3,3-tetrafluoropropyloxy)pyridineAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 31347SulfolaneLösungsmittelHCID 22335286Ethyl acetate pentaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a mixture of 2,2,3,3-tetrafluoropropan-1-ol (0.29 g, 2.2 mmol) in dry sulfolane (2 ml) is added NaH (60% in oil, 0.09 g, 2.2 mmol) and 2,6-bis-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridine (0.8 g, 1.8 mmol). After stirring at 110° C. for 3.7 h the mixture is cooled to ambient temperature. The resulting mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed 10 times with water. The organic layer is dried with 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 (0.72 g, 57% yield) of m.p. 73-74° C.

Aufarbeitung

  1. temperatureis cooled to ambient temperature
  2. filtrationfiltered through a bed of silica gel
  3. washThe filtrate is washed 10 times with water
  4. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-facc9139d28f472d8d74f9b9d1df1032
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852673B2

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