Water → Diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate

Temperature

0 °C

Anhydrous tetrahydrofuran (200 ml) was added to 60% sodium hydride (2.78 g, 69.52 mmol) and the resulting mixture was cooled to 0° C. Diethyl malonate (12.18 ml, 80.22 mmol) was slowly added dropwise to this mixture, which was then stirred for 1 hour at room temperature. A solution of 1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane (20.0 g, 53.48 mmol) 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=1/50) to give diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate (19.4 g, Yield 89%).

1. stirringby stirring for 12 hours at room temperature
2. extractionwas then extracted twice with ethyl acetate
3. washThe combined organic layers were washed with water and saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationAfter distilling off the solvent
6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/50)

ORD record

ord-f13162710fcc429e95b1be492588b701

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06552069B1