Ethyl Acetate → 5-Vinylnicotinonitrile

HRID 606827

Reaktionsgleichung

Reaktionsgleichung von HRID 606827
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.Br[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=1)[C:22]#[N:23].[Cl-].[NH4+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]([C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=1)[C:22]#[N:23])=[CH2:2]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 81998TributylvinyltinHCID 7367935-Bromonicotinonitrile

Produkt 1

HCID 670475755-VinylnicotinonitrileAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419050HCID 178419050, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Add bis(triphenylphosphine)palladium (II) dichloride (0.460 g, 0.66 mmol) and tributyl-vinyl-stannane (7.2 mL, 24.6 mmol) to a solution of 5-bromonicotinonitrile (3.0 g, 16.4 mmol) in toluene (50 mL) and stir at 110° C. for 150 min. Add an aqueous saturated solution of ammonium chloride and ethyl acetate and separate the layers. Wash the organic layer twice with an aqueous saturated solution of potassium fluoride and once with water. Dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with 3:1 hexane:ethyl acetate, to give the title compound (1.5 g, 70%).

Aufarbeitung

  1. customseparate the layers
  2. washWash the organic layer twice with an aqueous saturated solution of potassium fluoride
  3. dry with materialDry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 3:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-56b43414d3494c388f5d80d9389fb119
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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