Sodium Hydroxide → (Z)-2-(4-chloro-2-fluoro-phenyl)-5,5-dimethyl-hex-2-enenitrile

HRID 909006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909006
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[C:4]([F:11])[CH:3]=1.[CH3:12][C:13]([CH3:18])([CH3:17])[CH2:14][CH:15]=O.[OH-].[Na+]>CC(O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5](/[C:6](=[CH:15]/[CH2:14][C:13]([CH3:18])([CH3:17])[CH3:12])/[C:7]#[N:8])=[C:4]([F:11])[CH:3]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 763353,3-DimethylbutanalHCID 2736569(4-Chloro-2-fluoro-phenyl)-acetonitrile

Produkt 1

HCID 58222872(Z)-2-(4-chloro-2-fluoro-phenyl)-5,5-dimethyl-hex-2-enenitrileAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-2-fluoro-benzyl cyanide (Oakwood) (1.70 g, 10.0 mmol) and 3,3-dimethyl-butyraldehyde (Aldrich) (1.0 g, 10.0 mmol) in iPrOH (20 mL) was added 2 N NaOH (2.0 mL) dropwise at rt and the reaction mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc and the organic layer was separated, washed with water, brine, dried over Na2SO4 and concentrated. The residue was dried overnight in vacuum to give (Z)-2-(4-chloro-2-fluoro-phenyl)-5,5-dimethyl-hex-2-enenitrile (2.52 g, 100%) as a colorless oil which was used in the next step without further purification.

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was dried overnight in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ea27718fa3c54615ae83a5cd6d291c9a
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017607B2

Notizen zur Reaktion

Wird geladen…