Potassium Fluoride → 4-(1-Ethoxyvinyl)-2-fluoro-3-pyridinecarbaldehyde

HRID 1635069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1635069
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH2:11]([O:13][C:14]([Sn](CCCC)(CCCC)CCCC)=[CH2:15])[CH3:12].[F-].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:14]([O:13][C:11]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[C:7]=1[CH:8]=[O:9])=[CH2:12])[CH3:15]

Komponenten

6

Edukt 3

HCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 99923282-Fluoro-4-iodopyridine-3-carbaldehyde

Produkt 1

HCID 227450184-(1-Ethoxyvinyl)-2-fluoro-3-pyridinecarbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

There are mixed in succession 8 g (31.9 mmol) of 2-fluoro4-iodo-3-pyridinecarbaldehyde (described in J.O.C, 1993, 58, pp. 7832), 12.7 g (35.96 mmol) of 1-ethoxyvinyltributyltin and 740 mg of tetrakis(triphenylphosphine)palladium (2% molar) in 280 ml of dioxane. The reaction mixture is heated at reflux until the starting material has disappeared completely. After returning to room temperature, a solution of potassium fluoride is added to the reaction mixture. Vigorous stirring is maintained for 10 minutes in order to cause precipitation of the tributyltin fluoride, which is filtered off. The filtrate is plunged into a sodium chloride solution. The aqueous phase is extracted 3 times with dichloromethane and then the organic phases are combined, dried over magnesium sulphate, concentrated and purified by chromatography over a silica column, using a dichloromethane/cyclohexane mixture (95/5) as eluant to yield the expected product.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux until the starting material
  3. customAfter returning to room temperature
  4. temperatureis maintained for 10 minutes in order
  5. customprecipitation of the tributyltin fluoride, which
  6. filtrationis filtered off
  7. extractionThe aqueous phase is extracted 3 times with dichloromethane
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated
  10. custompurified by chromatography over a silica column

Quellen und Nachweise

ORD-Eintrag
ord-3e9eb35cab774120ac8cd3c7847b38f8
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509345B2

Notizen zur Reaktion

Wird geladen…