反応 #164822

反応方程式

Benzyl bromide

sodium hydroxide

water

1,7-Diphenyl-1,6-heptadiene-3,5-dione

→

white solid

収率 121.7%

4,4-Dibenzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione

収率 121.7%

溶媒

dichloromethane

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred for 1 hr at 40° C
2. 2
   温度The resulting mixture was cooled to room temperature
3. 3
   洗浄washed with saturated sodium chloride
4. 4
   乾燥dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他to afford a solid
8. 8
   その他The crude solid was chromatographed on silica gel with ethyl acetate/hexane
9. 9
   その他to give a solid
10. 10
    その他The solid was recrystallized from methanol

実験手順

1,7-Diphenyl-1,6-heptadiene-3,5-dione (3b, 0.25 g, 0.9 mmol) was stirred in dichloromethane (4 ml) for 5 min at room temperature. A solution of sodium hydroxide (80.0 mg, 2.0 mmol), tetrabutylammonium chloride (0.29 g, 1.0 mmol) and water (2 ml) was added and the mixture stirred for 10 min at room temperature. Benzyl bromide (10, 0.22 ml, 1.8 mmol) was added and the mixture stirred for 1 hr at 40° C. The resulting mixture was cooled to room temperature, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to give a solid. The solid was recrystallized from methanol to give 0.25 g (61%) of a white solid: mp 182-183° C. [expected mp 181° C.]; 1H NMR: δ 3.39 (s, 4H), 6.70 (d, 2H, J=15.5 Hz), 7.09-7.44 (m, 20H), 7.73 (d, 2H, J=15.5 Hz); 13C NMR: δ 37.7, 70.3, 123.1, 126.7, 128.1, 128.6, 128.8, 130.3, 130.7, 134.2, 136.3, 142.7, 196.8.

出典