Trimethylsilyl iodide → 7-(2,4,5-Triphenylimidazol-1-yl)heptane-phosphonic acid

HRID 265396Notes

Reaction equation

HRID 265396 reaction equation
[C:1]1([C:7]2[N:8]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][P:31]([O:36]CC)(=[O:35])[O:32]CC)[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](I)(C)C>C(Cl)(Cl)Cl>[C:1]1([C:7]2[N:8]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][P:31]([OH:36])(=[O:32])[OH:35])[C:9]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 22916421Diethyl 7-(2,4,5-triphenylimidazol-1-yl)heptane-phosphonate

Product 1

HCID 99345847-(2,4,5-Triphenylimidazol-1-yl)heptane-phosphonic acidYield 51.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-40 °C

Procedure

Diethyl 7-(2,4,5-triphenylimidazol-1-yl)heptane-phosphonate (0.35 g) was dissolved in dry chloroform, cooled to -40° C. and to it was added trimethylsilyl iodide (0.66 g) over 2 minutes under an atmosphere of nitrogen. The cooling bath was removed and the reaction mixture was stirred for 3 hours at room temperature then evaporated to an oil and revaporated evaporated from methanol and water respectively. The oil was taken up in methanol, treated with excess aqueous sodium bicarbonate, evaporated to dryness then taken up in ethanol, filtered and the filtrate evaporated to an oil. This was taken up in water, filtered and dilute hydrochloric acid added to pH4. The precipitated oil was washed with water, taken up in methanol and precipitated with ether to give 7-(2,4,5-triphenylimidazol-1-yl)heptane-phosphonic acid (0.16 g, 51%) as a light brown oil. Found: C, 68.12; H, 6.39, N, 5.60% C28H31N2O3P+4% H2O requires: C, 68.03; H 6.76); N, 5.66%.

Workup

  1. customThe cooling bath was removed
  2. customthen evaporated to an oil
  3. customrevaporated evaporated from methanol and water respectively
  4. additiontreated with excess aqueous sodium bicarbonate
  5. customevaporated to dryness
  6. filtrationfiltered
  7. customthe filtrate evaporated to an oil
  8. filtrationfiltered
  9. additiondilute hydrochloric acid added to pH4
  10. washThe precipitated oil was washed with water
  11. customprecipitated with ether

Sources & evidence

ORD record
ord-c994dd95ccb141b9b15223e20c7b976c
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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