Реакция #164822

Уравнение реакции

Benzyl bromide

sodium hydroxide

water

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

→

white solid

Выход 121.7%

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

Выход 121.7%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture stirred for 1 hr at 40° C
2. 2
   ТемператураThe resulting mixture was cooled to room temperature
3. 3
   Промывкаwashed with saturated sodium chloride
4. 4
   Сушкаdried over magnesium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated
7. 7
   Другоеto afford a solid
8. 8
   ДругоеThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
9. 9
   Другоеto give a solid
10. 10
    ДругоеThe solid was recrystallized from methanol

Методика

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.

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