Potassium Fluoride → 3,4',4''-Tri(diethoxyphosphoryl)-[2,2';5',2'']-terthiophene

HRID 1662887노트

반응식

HRID 1662887 반응식
[CH2:1]([O:3][P:4]([C:9]1[CH:10]=[C:11]([C:14]2[S:15][C:16](I)=[CH:17][C:18]=2[P:19]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[O:20])[S:12][CH:13]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C([Sn](CCCC)(CCCC)[C:33]1[S:34][CH:35]=[CH:36][C:37]=1[P:38]([O:43][CH2:44][CH3:45])([O:40][CH2:41][CH3:42])=[O:39])CCC.[Cu]C#N.[F-].[K+]>C1(C)C=CC=CC=1>[CH2:22]([O:21][P:19]([C:18]1[CH:17]=[CH:16][S:15][C:14]=1[C:11]1[S:12][C:13]([C:35]2[S:34][CH:33]=[C:37]([P:38]([O:40][CH2:41][CH3:42])([O:43][CH2:44][CH3:45])=[O:39])[CH:36]=2)=[C:9]([P:4]([O:6][CH2:7][CH3:8])([O:3][CH2:1][CH3:2])=[O:5])[CH:10]=1)([O:24][CH2:25][CH3:26])=[O:20])[CH3:23]

참가 물질

6

반응물 4

HCID 522689Potassium FluorideHCID 59155833HCID 59155833, 화합물HCID 591558664,3'-Bis(diethoxyphosphoryl)-5'-iodo-[2,2']-bithiopheneHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 591558983,4',4''-Tri(diethoxyphosphoryl)-[2,2';5',2'']-terthiophene수율 70%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

At room temperature, 0.1129 g (0.2 mmols) of 4,3′-bis(diethoxyphosphoryl)-5′-iodo-[2,2′]-bithiophene and 0.0092 g (0.008 mmols) of commercially available tetrakistriphenylphosphine palladium were dissolved in 2 ml of toluene, to which 0.1018 g (0.2 mmols) of 2-(tributylstannyl)-3-(diethoxyphosphoryl)thiophene and 0.0036 g (0.04 mmols) of commercially available copper(I) cyanide were added at room temperature. Thereafter, the reaction mixture was heated and stirred under reflux for 2.5 hours. After the reaction, the reaction mixture was cooled down to room temperature, to which a potassium fluoride aqueous solution added, followed by stirring for 1 hour. The resulting solid was removed by celite filtration and the filtrate was extracted with ethyl acetate. The 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 PTLC plate (developed with ethyl acetate:hexane=1:2 and ethyl acetate:hexane=1:1) to obtain the specified substance in the form of a yellow oil at a yield of 0.0919 g (yield: 70%).

후처리

  1. additionwere added at room temperature
  2. temperatureThereafter, the reaction mixture was heated
  3. temperatureunder reflux for 2.5 hours
  4. customAfter the reaction
  5. additionadded
  6. stirringby stirring for 1 hour
  7. customThe resulting solid was removed by celite filtration
  8. extractionthe filtrate was extracted with ethyl acetate
  9. washThe 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 PTLC plate (developed with ethyl acetate:hexane=1:2 and ethyl acetate:hexane=1:1)
  14. customto obtain the specified substance in the form of a yellow oil at a yield of 0.0919 g (yield: 70%)

출처 및 근거

ORD 기록
ord-ce0d56b2d4ad4e47901722c560466730
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030438B2

반응 노트

불러오는 중…