Reacción #704791

Ecuación de reacción

2-(4-benzyloxyphenyl)ethyl iodide

water

Diethyl ethylmalonate

sodium hydride

→

compound

Rendimiento 94.5%

Diethyl 2-ethyl-2-(2-(4-benzyloxyphenyl)ethyl)malonate

Rendimiento 94.5%

Disolventes

dimethylformamide

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe whole mixture was stirred at 0° C. for 20 minutes
2. 2
   workup.WAITto stand at room temperature overnight
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe ethyl acetate layer was washed with water
5. 5
   Secadoa saturated brine and dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled away under reduced pressure
7. 7
   Otrothe residue obtained
8. 8
   Otrowas purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9)

Procedimiento

Diethyl ethylmalonate (50 g) was added to a suspension of sodium hydride (11 g) in dimethylformamide (200 ml) and tetrahydrofuran (50 ml), at 0° C., and the mixture was stirred at room temperature for 35 minutes. A solution of 2-(4-benzyloxyphenyl)ethyl iodide (90 g) was added to the reaction mixture at 0° C. and the whole mixture was stirred at 0° C. for 20 minutes and allowed to stand at room temperature overnight. The resultant mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=1:9) to give the subject compound (100 g).

Fuente