Triethyl phosphonoacetate → 2,2-Bis(8-iodooctyl)-diethylphosphonoacetic acid ethyl ester

HRID 1285021Notes

Reaction equation

HRID 1285021 reaction equation
[H-].[Na+].[CH2:3]([O:5][P:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].I[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][I:26]>O1CCCC1>[CH2:15]([O:14][C:12](=[O:13])[C:11]([P:6]([O:5][CH2:3][CH3:4])([O:8][CH2:9][CH3:10])=[O:7])([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][I:26])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][I:26])[CH3:16]

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 906051,8-Diiodooctane

Product 1

HCID 136686282,2-Bis(8-iodooctyl)-diethylphosphonoacetic acid ethyl esterYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.96 g (0.02 mol) of sodium hydride was added to 40 ml of dry tetrahydrofuran, and to this solution was added dropwise under reflux a mixed solution of 1.34 g (6 mmol) of ethyl diethylphosphonoacetate and 11 g (0.03 mol) of 1,8-diiodooctane, and the solution was refluxed under heating for 4 hours. After distilling off tetrahydrofuran, the residue was cooled to room temperature, added with 1N hydrochloric acid until the litmus paper came to show acidity of the solution and then extracted three times with 50 ml of ether. After drying the extract over anhydrous sodium sulfate, ether was distilled off and the obtained oily residue was refined by passing through a basic alumina(activity II)-packed column using benzene-ethyl acetate (2:1) as eluent to obtain 1.76 g of 2,2-bis(8-iodooctyl)-diethylphosphonoacetic acid ethyl ester, ##STR35## (yield: 42%).

Workup

  1. additionto this solution was added dropwise
  2. temperaturethe solution was refluxed
  3. temperatureunder heating for 4 hours
  4. distillationAfter distilling off tetrahydrofuran
  5. additionadded with 1N hydrochloric acid until the litmus paper
  6. extractionextracted three times with 50 ml of ether
  7. customAfter drying the
  8. extractionextract over anhydrous sodium sulfate, ether
  9. distillationwas distilled off

Sources & evidence

ORD record
ord-6c985a7f55334d4a93b8aa9ec84b27df
Source dataset
uspto-grants-1986_01
Patent number
US04564690

Reaction notes

Loading…