Cesium carbonate → 3-(3-Cyanophenyl)4-cyclobutyl-butan-2-one

HRID 30388

Reaktionsgleichung

Reaktionsgleichung von HRID 30388
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([CH3:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH:13]1(Br)[CH2:16][CH2:15][CH2:14]1.[C:18](=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH2:18][CH:13]2[CH2:16][CH2:15][CH2:14]2)[C:10](=[O:11])[CH3:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 78110BromocyclobutaneHCID 133549593-(2-Oxopropyl)benzonitrile

Produkt 1

HCID 222707633-(3-Cyanophenyl)4-cyclobutyl-butan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 1.45 g (9.07 mmol) of 1-(3-cyanophenyl)acetone in 18 mL acetonitrile, 1.1 mL (9.5 mmol) cyclobutyl bromide and 5.91 g (18.1 mmol) cesium carbonate were added. After heating the solution in a 60° C. bath overnight, it was cooled and filtered. The filtrate was partitioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated. The residue was purified on a flash column using a gradient of 5-10% EtOAc/hexane to isolate the title compound. 1H NMR: (500 MHz, CDCl3): δ 1.5-2.2 (m, 9H), 2.13 (s, 3H), 3.64 (m, 1H), 7.4-7.7 (m, 4H).

Aufarbeitung

  1. temperaturewas cooled
  2. filtrationfiltered
  3. customThe filtrate was partitioned between water and EtOAc
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified on a flash column

Quellen und Nachweise

ORD-Eintrag
ord-b35b30713ad8435ca0fdaf1c324a6c9c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423067B2

Verknüpfte Notizen

Wird geladen…