Acetone → 1,5-Bis(3-fluorophenyl)-1,4-pentadien-3-one

HRID 77656

Reaktionsgleichung

Reaktionsgleichung von HRID 77656
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:10][C:11](=[O:12])[CH:13]=[CH:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 680093-Fluorobenzaldehyde

Produkt 1

HCID 695017221,5-Bis(3-fluorophenyl)-1,4-pentadien-3-oneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3-Fluorobenzaldehyde (1s, 0.5 ml, 4.7 mmol) and acetone (19, 0.18 ml, 2.3 mmol) were combined in ethanol (20 ml) and stirred for 10 min at room temperature. A solution of sodium hydroxide (0.29 g, 7.3 mmol) and water (15 ml) was added and the mixture stirred for 18 hr at room temperature. The resulting mixture was filtered and chromatographed on silica gel with ethyl acetate/hexane to give a solid. The crude was recrystallized from ethanol to afford 0.26 g (42%) of yellow crystals: mp 96-97° C. [expected mp 96-97° C.]; 1H NMR: δ 7.03 (d, 2H, J=16.1 Hz), 7.09 (m, 2H), 7.35 (m, 6H), 7.67 (d, 2H, J=15.9 Hz); 13C NMR: δ 114.4, 117.5, 124.4, 126.3, 130.4, 136.9, 142.0, 162.9, 188.1; Anal. Calcd for C17H12OF2: C, 75.55; H, 4.48. Found: C, 75.26; H, 4.65.

Aufarbeitung

  1. stirringthe mixture stirred for 18 hr at room temperature
  2. filtrationThe resulting mixture was filtered
  3. customchromatographed on silica gel with ethyl acetate/hexane
  4. customto give a solid
  5. customThe crude was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b896188ea0824f719c74a4f42878ee58
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841326B2

Verknüpfte Notizen

Wird geladen…