Ethyl Acetate → 4-(4-Chlorophenyl)-3-cyano-3-phenyl-2-butanone

HRID 1394570

Reaktionsgleichung

Reaktionsgleichung von HRID 1394570
[C:1]([CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:5]#[N:6])(=[O:3])[CH3:2].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C(#N)C.O>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][C:4]([C:5]#[N:6])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:1](=[O:3])[CH3:2])=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 20547Alpha-phenylacetoacetonitrileHCID 693291-(Bromomethyl)-4-chlorobenzene

Produkt 1

HCID 664309254-(4-Chlorophenyl)-3-cyano-3-phenyl-2-butanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of α-acetylphenylacetonitrile (1.0 g, 6.3 mmol) in acetonitrile (25 mL) was added 4-chlorobenzyl bromide (1.3 g, 6.3 mmol) and cesium carbonate (8.2 g, 25 mmol). After stirring at room temperature for 2 h, the reaction mixture was poured into ethyl acetate (100 mL) and water (100 mL). The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to dryness, and the residue was purified on a silica gel column eluting with 1 to 5% ethyl acetate in hexane to give the title compound. 1H NMR (400 MHz, CD3OD): δ 7.5-6.9 (m, 9H), 3.56 (d, 1H), 3.37 (d, 1H), 2.22 (s, 3H). LC-MS: m/e 306 (M+Na)+ (3.0 min).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customthe residue was purified on a silica gel column
  7. washeluting with 1 to 5% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-5350ab1fab1343108b62ec94ee75f8ca
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348456B2

Verknüpfte Notizen

Wird geladen…