Piperidine → (E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate

HRID 333326

Reaktionsgleichung

Reaktionsgleichung von HRID 333326
[C:1]([CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2].[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH:15]=O.N1CCCCC1>CCO>[C:1](/[C:3](=[CH:15]\[C:14]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:12]([Cl:11])[CH:13]=1)/[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 227103,4-DichlorobenzaldehydeHCID 70693tert-Butyl cyanoacetate

Produkt 1

HCID 68751356(E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylateAusbeute 81,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of tert-butyl cyanoacetate (2.52 ml, 17.63 mmol), 3,4-dichlorobenzaldehyde (2.57 g, 14.69 mmol) and piperidine (0.145 ml, 1.469 mmol) in EtOH (50 ml) was allowed to stir at 80° C. for 15 hours, and then cooled to ambient temperature. A half volume of the solvent was evaporated, and 400 ml of water was added to the resulting mixture. The precipitated solid was collected and washed with 5% iPrOH/H2O (200 ml). The solid was dried under reduced pressure to give (E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate (3.577 g); Retention time=1.61 minutes (condition A); MS (ES+)=315.1 (m+18).

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. customA half volume of the solvent was evaporated
  3. addition400 ml of water was added to the resulting mixture
  4. customThe precipitated solid was collected
  5. washwashed with 5% iPrOH/H2O (200 ml)
  6. customThe solid was dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1491605790b04672bdfb6bed058d5069
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877815B2

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