Diethyl(1,1-difluoro-3-butenyl)phosphonate → [4-(Diethoxymethylsilyl)-1,1-difluoro-butyl]-phosphonic acid diethyl ester

HRID 351192Notes

Reaction equation

[CH2:1]([O:3][P:4]([C:9]([F:14])([F:13])[CH2:10][CH:11]=[CH2:12])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[CH2:15]([O:17][CH:18]([SiH3:22])[O:19][CH2:20][CH3:21])[CH3:16]>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][P:4]([C:9]([F:14])([F:13])[CH2:10][CH2:11][CH2:12][SiH2:22][CH:18]([O:19][CH2:20][CH3:21])[O:17][CH2:15][CH3:16])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

5 g (23.4 mmol) diethyl-1,1-difluorobut-3-enylphosphonate was mixed with 7.5 g (56 mmol) diethoxymethylsilane and several drops of hydrogen hexachloroplatinate (IV) solution (5% in isopropanol). After stirring at 60° C. overnight, the solution was evaporated under reduced pressure to remove the reactants and product [4-(diethoxymethylsilyl)-1,1-difluoro-butyl]-phosphonic acid diethyl ester (DMSFP, 6 g, 16.6 mmol, yield 71%) was provided. See Scheme 7. 1H NMR (CDCl3): δ(ppm) 0.12(3H, s), 0.65 (2H, m), 1.21 (6H, t, JH-H=6.98), 1.35 (6H, 6, JH-H=7.06), 1.65 (2H,m), 2.15 (2H,m), 3.75 (4H, q, JH-H=6.98), 4.26 (4H, q, JH-H=7.06).

Workup

customthe solution was evaporated under reduced pressure
customto remove the reactants

Sources & evidence

ORD record: ord-b0b29e92ce3c41faa0fe7eba44e5b31d
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183370B2

Reaction notes

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