Reacción #1354933

Ecuación de reacción

Water

7-Iodo-1-heptene

Sodium hydride

diethyl malonate

→

diethyl 2-(6-heptenyl)malonate

Rendimiento 84.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas then slowly added dropwise to the mixture
2. 2
   workup.STIRRINGby stirring for 12 hours at room temperature
3. 3
   Extracciónwas then extracted twice with ethyl acetate
4. 4
   LavadoThe combined organic layers were washed with water and saturated aqueous sodium chloride
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONAfter distilling off the solvent
7. 7
   Otrothe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/40)

Procedimiento

Sodium hydride (60%, 5.78 g, 144.59 mmol) was added to anhydrous tetrahydrofuran (250 ml) and cooled to 0° C. To this mixture, diethyl malonate (25.09 g, 156.64 mmol) was slowly added dropwise, followed by stirring for 1 hour at room temperature. 7-Iodo-1-heptene (27 g, 120.49 mmol) dissolved in anhydrous tetrahydrofuran (50 ml) was then slowly added dropwise to the mixture, followed by stirring for 12 hours at room temperature. Water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/40) to give diethyl 2-(6-heptenyl)malonate (25.8 g, Yield 84%).

Fuente