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

HRID 2354494
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2354494
Br[Si](C)(C)C.C[O:7][P:8]([CH2:12][P:13]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28])([O:15]CC)=[O:14])(=[O:11])[O:9]C.C(N(CCCC)CCCC)CCC.[Na+:42].[I-].CC(C)=O>CO>[Na+:42].[Na+:42].[Na+:42].[CH2:18]([P:13]([CH2:12][P:8](=[O:7])([O-:11])[O-:9])([OH:15])=[O:14])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]=[CH2:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 7622TributylamineHCID 76113BromotrimethylsilaneHCID 21054117((10-Undecenyl)-ethoxyphosphinyl)methylphosphonic acid dimethyl ester

Produkt 1

HCID 131725942((10-Undecenyl)-hydroxyphosphinyl)methylphosphonic acid tri sodium salt
Ausbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ae7e33db8c924605b4d9899eaa31a78e
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07754200B2

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