Reacción #1248

Ecuación de reacción

2', 4', 6'-trimethylacetophenone

diethyl oxalate

NaH

→

red oil

Rendimiento 66.7%

Ethyl 2,4-dioxo-4-(2,4,6-trimethylphenyl)butanoate

Rendimiento 66.7%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was slowly heated
2. 2
   Temperaturato reflux under N2
3. 3
   TemperaturaIt was refluxed for about 20 minutes
4. 4
   Temperaturacooled
5. 5
   workup.ADDITIONpoured into ice-cold aqueous HCl solution
6. 6
   Extracciónextracted with ether
7. 7
   LavadoThe extracts were washed with brine
8. 8
   Secadodried over Na2SO4
9. 9
   Filtraciónfiltered through a short silica gel pad
10. 10
    Concentraciónconcentrated

Procedimiento

To a solution of 2', 4', 6'-trimethylacetophenone (15 g, 92.6 mmol) and diethyl oxalate (20 g, 139 mmol) in 500 mL of anhydrous toluene was cautiously added 7.4 g of NaH (60% dispersion in mineral oil). The reaction mixture was slowly heated to reflux under N2. It was refluxed for about 20 minutes, then cooled, poured into ice-cold aqueous HCl solution, and extracted with ether. The extracts were washed with brine, dried over Na2SO4, filtered through a short silica gel pad and concentrated to give 16.2 g of a red oil which was used in the next reaction without further purification.

Fuente