Methoxymethyl-triphenylphosphonium chloride → 5-(4,4,4-Trifluoro-1-methoxymethylene-butyl)-2-(4-trifluoromethyl-phenyl)-pyridine

HRID 1669305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669305
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[F:30][C:31]([F:53])([F:52])[CH2:32][CH2:33][C:34]([C:36]1[CH:37]=[N:38][C:39]([C:42]2[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][CH:43]=2)=[CH:40][CH:41]=1)=O>C1(C)C=CC=CC=1>[F:30][C:31]([F:53])([F:52])[CH2:32][CH2:33][C:34]([C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([C:48]([F:51])([F:50])[F:49])=[CH:44][CH:43]=2)=[N:38][CH:37]=1)=[CH:2][O:3][CH3:4]

Komponenten

5

Edukt 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 860853424,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one

Produkt 1

HCID 866203565-(4,4,4-Trifluoro-1-methoxymethylene-butyl)-2-(4-trifluoromethyl-phenyl)-pyridineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Methoxymethyltriphenylphosphonium chloride (7.4 g, 21.6 mmol) is suspended in anhydrous toluene (25 mL) and potassium tert-butoxide (2.4 g, 21.6 mmol) is added at room temperature in one portion. The mixture is allowed to stir under nitrogen for 1 h. Meanwhile, 4,4,4-Trifluoro-1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-one (5.0 g, 14.4 mmol) is dissolved in another portion of the toluene (25 mL), and kept at room temperature. The mixture is then cooled to 0° C. with ice water, and then the ketone is transferred by cannula. The reaction is allowed to stir at 0° C. for 10 min, then the ice bath is removed. The reaction is allowed to warm to room temperature and monitored by HPLC. Upon complete conversion, the reaction is carefully quenched with saturated ammonium chloride solution, and diluted with ethyl acetate, then extracted. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate, then filtered and concentrated. The 5-(4,4,4-Trifluoro-1-methoxymethylene-butyl)-2-(4-trifluoromethyl-phenyl)-pyridine (4.1 g, 10.9 mmol) is isolated as a mixture of regioisomers after column chromatography, 76% yield.

Aufarbeitung

  1. customkept at room temperature
  2. stirringto stir at 0° C. for 10 min
  3. customthe ice bath is removed
  4. customUpon complete conversion, the reaction is carefully quenched with saturated ammonium chloride solution
  5. additiondiluted with ethyl acetate
  6. extractionextracted
  7. washThe organic layer is washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8ca8966499164488afebb657ea266451
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989457B2

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