Reacción #164838

Ecuación de reacción

3-Fluorobenzaldehyde

acetone

sodium hydroxide

water

→

yellow crystals

Rendimiento 42.0%

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

Rendimiento 42.0%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture stirred for 18 hr at room temperature
2. 2
   FiltraciónThe resulting mixture was filtered
3. 3
   Otrochromatographed on silica gel with ethyl acetate/hexane
4. 4
   Otroto give a solid
5. 5
   OtroThe crude was recrystallized from ethanol

Procedimiento

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.

Fuente