Ethyl cyanoacetate → Ethyl 3-(4-chloro-3-fluorophenyl)-2-cyanoacrylate

HRID 1675837

Reaktionsgleichung

Reaktionsgleichung von HRID 1675837
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[F:10].[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12].N1CCCCC1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:13]([C:11]#[N:12])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4][C:3]=1[F:10]

Komponenten

5

Edukt 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 27249854-Chloro-3-Fluorobenzaldehyde

Produkt 1

HCID 67338173Ethyl 3-(4-chloro-3-fluorophenyl)-2-cyanoacrylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-Chloro-3-fluorobenzaldehyde (1.0 g, 6.3 mmol) was added to a solution of ethyl 2-cyanoacetate (0.71 g, 6.3 mmol) and piperidine (0.081 ml, 0.82 mmol) in toluene (10 mL) at room temperature. The mixture was heated at 100° C. for 7 hours. Upon cooling to room temperature, the mixture was concentrated in vacuo and rinsed with hexane to give ethyl 3-(4-chloro-3-fluorophenyl)-2-cyanoacrylate (1.4 g, 88%). LCMS (APCI+) [M+H]+ 253.1.

Aufarbeitung

  1. temperatureUpon cooling to room temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. washrinsed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-63ac80f4255645b9b0a522370885bdb5
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003651B2

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