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

HRID 1285021ノート

反応式

HRID 1285021 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6c985a7f55334d4a93b8aa9ec84b27df
出典データセット
uspto-grants-1986_01
特許番号
US04564690

反応ノート

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