تفاعل #440274

معادلة التفاعل

Sodium iodide

3,5-dimethylbenzyl bromide

3,5-heptanedione

sodium hydride

→

title compound

المردود 44.2%

4-(3,5-Dimethylbenzyl)-3,5-heptanedione

المردود 44.2%

المذيبات

2-butanone

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGwas stirred at room temperature for 18 hours
2. 2
   تركيزThe solution was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
4. 4
   غسيلwashed with water (×3)
5. 5
   تجفيفThe organic phase was dried over anhydrous magnesium sulphate
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated under reduced pressure
8. 8
   أخرىThe crude product was purified by flash chromatography on silica gel eluting with cyclohexane

الإجراء التجريبي

A solution of 3,5-heptanedione (1.24 ml, 9.13 mmol) in 2-butanone (40 ml) was treated with sodium hydride (60% dispersion in oil) (402 mg, 10.05 mmol) (added in portions) and stirred at room temperature for 10 minutes. Sodium iodide (1.5 g, 10.05 mmol) and then by 3,5-dimethylbenzyl bromide (2.0 g, 10.05 mmol) were added to the reaction mixture which was stirred at room temperature for 18 hours. The solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water (×3). The organic phase was dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with cyclohexane followed by cyclohexane:ethyl acetate (40:1, by volume) to afford the title compound as a yellow oil (995 mg).

المصدر