Reaktion #164822

Reaktionsgleichung

Benzyl bromide

sodium hydroxide

water

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

→

white solid

Ausbeute 121.7%

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

Ausbeute 121.7%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for 1 hr at 40° C
2. 2
   TemperaturThe resulting mixture was cooled to room temperature
3. 3
   Waschenwashed with saturated sodium chloride
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto afford a solid
8. 8
   SonstigeThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
9. 9
   Sonstigeto give a solid
10. 10
    SonstigeThe solid was recrystallized from methanol

Vorschrift

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.

Quelle