Reacción #1354657

Ecuación de reacción

water

sodium hydride

diethyl 2-(6-heptenyl)malonate

1-Iodo-4,4,5,5,6,6,7,7,7-nonafluoroheptane

→

diethyl 2-(6-heptenyl)-2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)malonate

Rendimiento 101.6%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGby stirring for 12 hours at room temperature
2. 2
   Extracciónwas then extracted with ethyl acetate
3. 3
   LavadoThe organic layer was washed with water and saturated aqueous sodium chloride
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONAfter distilling off the solvent
6. 6
   Otrothe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/25)

Procedimiento

60% sodium hydride (0.54 g, 13.5 mmol) was added to a solution of diethyl 2-(6-heptenyl)malonate (3.0 g, 11.7 mmol) in tetrahydrofuran (30 ml) followed by stirring for 30 minutes at room temperature. 1-Iodo-4,4,5,5,6,6,7,7,7-nonafluoroheptane (5.45 g, 14.04 mmol) was added to the mixture followed by stirring for 12 hours at room temperature. After the reaction was completed, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was 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=1/25) to give diethyl 2-(6-heptenyl)-2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)malonate (6.14 g, quantitative) as a colorless oil.

Fuente