Acetic Acid → 2-(4-Chlorobenzoyl)-3-methylhex-2-enenitrile

HRID 597828

Reaktionsgleichung

Reaktionsgleichung von HRID 597828
[CH3:1][C:2](=O)[CH2:3][CH2:4][CH3:5].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:18])[CH2:15][C:16]#[N:17])=[CH:10][CH:9]=1.NCCC(O)=O.C(O)(=O)C>CCOC(C)=O.C1(C)C=CC=CC=1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([C:15](=[C:2]([CH3:1])[CH2:3][CH2:4][CH3:5])[C:16]#[N:17])=[O:18])=[CH:12][CH:13]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 239Beta-AlanineHCID 78952-PentanoneHCID 1383084-Chlorobenzoylacetonitrile

Produkt 1

HCID 670546102-(4-Chlorobenzoyl)-3-methylhex-2-enenitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of pentan-2-one (20 mmol), 3-(4-chlorophenyl)-3-oxopropanenitrile (3.6 g, 20 mmol), β-alanine (180 mg, 2 mmol), acetic acid (2.6 mL) and toluene (60 mL) is heated to reflux in a Dean-Stark system for 18 h. The solution is cooled to RT, then diluted with EtOAc (50 mL), washed with 5% NaHCO3 (3×20 mL), water (20 mL), brine (20 mL), dried (Na2SO4) and finally concentrated in vacuo. A mixture of the two isomers is obtained as a colorless oil by chromatographic purification of the crude residue on silica gel using EtOAc:petroleum ether (0.5:9.5) as eluent.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux in a Dean-Stark system for 18 h
  3. washwashed with 5% NaHCO3 (3×20 mL), water (20 mL), brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationfinally concentrated in vacuo
  6. additionA mixture of the two isomers

Quellen und Nachweise

ORD-Eintrag
ord-40d212c38f51454c9755e7e451e5617c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897596B2

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