Potassium Carbonate → 4-[1-(Trifluoromethyl)ethenyl]pyridine

HRID 1880770

Reaktionsgleichung

Reaktionsgleichung von HRID 1880770
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:14][C:15]([F:22])([F:21])[C:16](B(O)O)=[CH2:17].[Cl-].[NH4+]>O1CCOCC1>[F:14][C:15]([F:22])([F:21])[C:16]([C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[CH2:17]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 6094924-IodopyridineHCID 2782677(3,3,3-Trifluoroprop-1-en-2-yl)boronic acid

Produkt 1

HCID 595703554-[1-(Trifluoromethyl)ethenyl]pyridineAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To 1,4-dioxane were added 3.22 g of 4-iodopyridine, 10.87 g of potassium carbonate, 0.036 g of tetrakis(triphenylphosphinepalladium) and 5.5 g of 1-(trifluoromethyl)vinylboronic acid, and the mixture was stirred at 110° C. for 8 hours. Thereafter, this solution was poured into an aqueous saturated ammonium chloride solution, followed by extraction with diethyl ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 2.0 g of 4-[1-(trifluoromethyl)ethenyl]pyridine.

Aufarbeitung

  1. extractionfollowed by extraction with diethyl ether three times
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9f0c2151f2b44a58a621a8a51def4c6e
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318776B2

Verknüpfte Notizen

Wird geladen…