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

HRID 333325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 333325
[C:1](/[C:3](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)/[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2]>CC(O)=O.C1(C)C=CC=CC=1.[Cl-].[Na+].O.[Zn]>[C:1]([CH:3]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[C:4]([O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:5])#[N:2]

Komponenten

6

Edukt 1

HCID 68751356(E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate

Produkt 1

HCID 68748010Tert-butyl 2-cyano-3-(3,4-dichlorophenyl)propanoateAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of (E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate (1.05 g, 3.52 mmol) and zinc (3.45 g, 52.8 mmol) in AcOH (20 ml) was allowed to stir at 100° C. After stirred for 1 hour, the reaction mixture was cooled to ambient temperature, and diluted with toluene and brine. The phases were separated, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give tert-butyl 2-cyano-3-(3,4-dichlorophenyl)propanoate (819 mg); Retention time=1.41 minutes (condition B); MS (ES+)=317.0 (m+18).

Aufarbeitung

  1. stirringAfter stirred for 1 hour
  2. temperaturethe reaction mixture was cooled to ambient temperature
  3. customThe phases were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4ac60e95d9b7405da0326c6a5336e5f7
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877815B2

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