반응 #164822

반응 방정식

Benzyl bromide

sodium hydroxide

water

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

→

white solid

수율 121.7%

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

수율 121.7%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture stirred for 1 hr at 40° C
2. 2
   온도The resulting mixture was cooled to room temperature
3. 3
   세척washed with saturated sodium chloride
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타to afford a solid
8. 8
   기타The crude solid was chromatographed on silica gel with ethyl acetate/hexane
9. 9
   기타to give a solid
10. 10
    기타The solid was recrystallized from methanol

실험 절차

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.

출처