Cyanoacetic acid → HCID 367315, Verbindung

HRID 589831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589831
[C:1]([CH2:3][C:4](O)=O)#[N:2].[F:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)C=O>C1(C)C=CC=CC=1.N1C=CC=CC=1>[F:7][C:8]1[CH:15]=[C:14]([CH:4]=[CH:3][C:1]#[N:2])[CH:13]=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 9740Cyanoacetic acidHCID 680093-Fluorobenzaldehyde

Produkt 1

HCID 367315HCID 367315, VerbindungAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 35.0 g (411 mmol) of cyanoacetic acid (CAS 372-09-8) and 56.2 g (453 mmol) of 3-fluorobenzaldehyde (CAS 456-48-4) in a mixture of 400 ml of toluene and 220 ml of pyridine is refluxed for 22 hours using Dean-Stark apparatus to remove the water formed during the reaction. The solvent is then removed under reduced pressure and the residue is co-evaporated 3 times with toluene. The residue is then taken up in ethyl acetate and the organic phase is washed successively with aqueous 1N sodium hydroxide solution, aqueous 1N hydrochloric acid solution and then with saturated sodium chloride solution. The organic phase is then dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give a brown oil, which is chromatographed on a column of silica gel, eluting with toluene, to give 48.5 g a mixture of (E) and (Z) 3-(3-fluorophenyl)-2-propenenitrile in a ratio of (7/3)

Aufarbeitung

  1. temperatureis refluxed for 22 hours
  2. customto remove the water
  3. customformed during the reaction
  4. customThe solvent is then removed under reduced pressure
  5. washthe organic phase is washed successively with aqueous 1N sodium hydroxide solution, aqueous 1N hydrochloric acid solution
  6. dry with materialThe organic phase is then dried over sodium sulfate
  7. customthe solvent is evaporated off under reduced pressure
  8. customto give a brown oil, which
  9. customis chromatographed on a column of silica gel
  10. washeluting with toluene

Quellen und Nachweise

ORD-Eintrag
ord-800c283c6caa4dfca7b9dcbcb0fa9d6a
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233965B2

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