Acetone → ((10-Undecenyl)-hydroxyphosphinyl)methylphosphonic acid tri sodium salt

Bromotrimethylsilane (0.8 mL, 6.06 mmol) was added dropwise to ((10-undecenyl)-ethoxyphosphinyl) methylphosphonic acid dimethyl ester (0.250 g, 0.68 mmol) in a 3 mL vial. This solution was stirred for 14–16 hours at ambient temperature. Excess bromotrimethylsilane was removed by passing a steady stream of dry nitrogen over the solution for 2 hours. The residue was then placed under high vacuum for 3 hours to remove residual bromotrimethylsilane. Tributylamine (0.57 g, 3.08 mmol) and methanol (3 mL) was then added to the residue resulting in a clear solution. This mixture was added dropwise to a 0.5 M solution of NaI in acetone (10 mL, 5.0 mmol). A white solid precipitated immediately. The solid was collected by centrifugation and the acetone solution was discarded. The solid was then washed by suspension in clean acetone (20 mL), centrifugation and removal of acetone supernatant. After this washing procedure was completed 3 times, the solid was placed under vacuum for a period of 12–16 hours providing the desired product (0.19 g, 74% yield). 1H NMR (400 MHz D2O): δ 5.8 (m, 1H), 4.9 (m, 2H), 1.9 (m, 4H), 1.6 (m, 2H) 1.2 (m, 14H).

1. customExcess bromotrimethylsilane was removed
2. customfor 2 hours
3. customto remove residual bromotrimethylsilane
4. customresulting in a clear solution
5. customA white solid precipitated immediately
6. customThe solid was collected by centrifugation
7. washThe solid was then washed by suspension in clean acetone (20 mL)
8. customcentrifugation and removal of acetone supernatant
9. waitthe solid was placed under vacuum for a period of 12–16 hours

ORD record

ord-b61433886c974300b98b0ebfc1e2ace9

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109184B2