Potassium Fluoride → 4,3'-Bis(diethoxyphosphoryl)-[2,2']-bithiophene

HRID 1662885ノート

反応式

HRID 1662885 の反応式
I[C:2]1[S:6][CH:5]=[C:4]([P:7]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:20]1[S:21][CH:22]=[CH:23][C:24]=1[P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])CCC.[F-].[K+]>C1(C)C=CC=CC=1.[Cu]Cl>[CH2:10]([O:9][P:7]([C:4]1[CH:3]=[C:2]([C:20]2[S:21][CH:22]=[CH:23][C:24]=2[P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[S:6][CH:5]=1)([O:12][CH2:13][CH3:14])=[O:8])[CH3:11]

参加物

6

反応物 3

HCID 522689Potassium FluorideHCID 59155826HCID 59155826、化合物HCID 59155833HCID 59155833、化合物

生成物 1

HCID 591558484,3'-Bis(diethoxyphosphoryl)-[2,2']-bithiophene収率 84%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 1140Toluene溶媒

実験手順

At room temperature, 1.4875 g (4.3 mmols) of 5-iodo-3-(diethoxyphosphoryl)thiophene and 0.0994 g (0.086 mmols) of commercially available tetrakistriphenylphosphine palladium were dissolved in 43 ml of toluene, to which 2.1899 g (4.3 mmols) of 2-tributylstannyl-3-(diethoxyphosphoryl)thiophene and 0.0347 g (0.39 mmols) of commercially available copper(I) chloride were added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 3.5 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a potassium fluoride aqueous solution was added, followed by stirring for 1 hour. Thereafter, the solid was removed by celite filtration and the filtrate was extracted with ethyl acetate. The resulting organic phase was washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was removed by distilling off under reduced pressure, and the resulting crude product was purified with a silica gel column (gradiated with acetone from ethyl acetate) to obtain the specified substance in the form of a yellow oil at a yield of 1.5836 g (yield: 84%).

後処理

  1. additionwere added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 3.5 hours
  4. customAfter the reaction
  5. additionwas added
  6. stirringby stirring for 1 hour
  7. customThereafter, the solid was removed by celite filtration
  8. extractionthe filtrate was extracted with ethyl acetate
  9. washThe resulting organic phase was washed with a saturated saline solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. customThe solvent was removed
  12. distillationby distilling off under reduced pressure
  13. customthe resulting crude product was purified with a silica gel column (gradiated with acetone from ethyl acetate)
  14. customto obtain the specified substance in the form of a yellow oil at a yield of 1.5836 g (yield: 84%)

出典と根拠

ORDレコード
ord-51a2383e42a741d4b7d7d4b6de79f52d
出典データセット
uspto-grants-2011_10
特許番号
US08030438B2

反応ノート

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