Triethyl phosphite → Diethyl 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecylphosphonate

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Reaction Conditions

Reaction Steps

1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-10-iododecane (1.02 g, 1.78 mmol) and P(OEt)3 (15 ml, excess) was added to 50 ml round bottom flask. The mixture was heated to 120° C. under nitrogen for 40 hours and then purified with FluoroFlash® SPE cartridge. The remaining light yellow oil was chromatographed with Ethyl Acetate/Hexane to give product. (0.96 g, 92%). 1H NMR (600 MHz, CDCl3): δ (ppm) 4.10-4.00(m, 4H, CH2CH3), 2.35-2.23 (m, 2H, CH2CF2), 1.92-1.86 (m, 2H, PCH2), 1.25 (t, J=7.2 Hz, 6H, CH2CH3). 13C NMR (150 MHz, CDCl3): δ (ppm) 121-106 (m, C—F coupling unsolved), 62.28 (d, 2Jcp=6 Hz, CH2CH3), 25.33 (t, 2JcF=23 Hz, CH2CF2), 17.24 (d, 2Jcp=148 Hz, PCH2), 16.38, 3Jcp=6 Hz, CH2CH3), HRMS calcd for C14H14F17O3P: [M+H]+, 585.0487; found: 585.0433

Provenance & Evidence