تفاعل #164822

معادلة التفاعل

Benzyl bromide

sodium hydroxide

water

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

→

white solid

المردود 121.7%

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

المردود 121.7%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture stirred for 1 hr at 40° C
2. 2
   درجة الحرارةThe resulting mixture was cooled to room temperature
3. 3
   غسيلwashed with saturated sodium chloride
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated
7. 7
   أخرىto afford a solid
8. 8
   أخرىThe crude solid was chromatographed on silica gel with ethyl acetate/hexane
9. 9
   أخرىto give a solid
10. 10
    أخرىThe solid was recrystallized from methanol

الإجراء التجريبي

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.

المصدر