Triethyl phosphonoacetate → HCID 86672774, compound

Temperature

0 °C

1,8-Diazabicyclo[5.4.0]undec-7-ene (1.08 mL, 7.26 mmol) was added to a solution of (diethoxy-phosphoryl)-acetic acid ethyl ester (1.57 mL, 7.87 mmol) and lithium chloride (359 mg, 8.47 mmol) in acetonitrile (60.5 mL) at 0° C., and the mixture was stirred at 0° C. for 10 minutes. A solution of 7,7,8,8,8-pentafluoro-octanal (1.32 g, 6.05 mmol) in acetonitrile (20.5 mL) was added dropwise to the reaction solution at 0° C., and the mixture was stirred for 10 minutes. Thereafter, the reaction mixture was stirred at room temperature for one hour and diluted with methyl tert-butyl ether (300 mL). The organic layer was sequentially washed with 2 N hydrochloric acid (50 mL), H2O (50 mL) and saturated brine (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give (E)-9,9,10,10,10-pentafluoro-dec-2-enoic acid ethyl ester (purity 80%) as a colorless oily substance (49.7 mg, 47%).

1. stirringthe mixture was stirred for 10 minutes
2. stirringThereafter, the reaction mixture was stirred at room temperature for one hour
3. washThe organic layer was sequentially washed with 2 N hydrochloric acid (50 mL), H2O (50 mL) and saturated brine (50 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

ORD record

ord-1a025e398adb415e91a0831c2039d4f9

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169254B2