反応 #164838

反応方程式

3-Fluorobenzaldehyde

acetone

sodium hydroxide

water

→

yellow crystals

収率 42.0%

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

収率 42.0%

溶媒

ethanol

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred for 18 hr at room temperature
2. 2
   ろ過The resulting mixture was filtered
3. 3
   その他chromatographed on silica gel with ethyl acetate/hexane
4. 4
   その他to give a solid
5. 5
   その他The crude was recrystallized from ethanol

実験手順

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.

出典