Toluene → Dimethyl-bis(2-methyl-1H-inden-1-yl)silane

HRID 1892887

반응식

HRID 1892887 반응식
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:18]([Li])[CH2:19][CH2:20]C.[CH3:23][Si:24]([CH3:27])(Cl)Cl>O.C1COCC1>[CH3:23][Si:24]([CH3:27])([CH:18]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:17]=[C:19]1[CH3:20])[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 6398DichlorodimethylsilaneHCID 165871H-Indene, 2-methyl-HCID 178418339Butyllithium

생성물 1

HCID 4050248Dimethyl-bis(2-methyl-1H-inden-1-yl)silane

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

8.0 g (61.4 mmoles) of 2-methylindene were introduced into 175 mL of toluene and 13 mL of THF, and 24.6 mL of n-butyllithium (2.5 M in toluene) were added without interruption at room temperature. After this addition was complete, the mixture was heated to 80° C. and stirred at this temperature for one hour. It was allowed to cool to 40° C., then 3.96 g (30.7 mmoles) of dimethyldichlorosilane were slowly added dropwise. After this addition, the reaction solution was stirred for three hours at 60° C. and then overnight at room temperature. 70 mL of water were added and the phases that form were separated. The organic phase was washed with 100 mL of water, and the aqueous phase was extracted three times with a total of 100 mL of toluene. The combined organic phases were dried over magnesium sulfate. After separation of the magnesium sulfate, the solvent was removed and the residue was purified by column chromatography. The desired product was isolated in a yield of 8.16 g (84%) (purity 99%).

후처리

  1. additionwere added without interruption at room temperature
  2. additionAfter this addition
  3. temperatureto cool to 40° C.
  4. additionAfter this addition
  5. stirringthe reaction solution was stirred for three hours at 60° C.
  6. customovernight
  7. customat room temperature
  8. customthe phases that form were separated
  9. washThe organic phase was washed with 100 mL of water
  10. extractionthe aqueous phase was extracted three times with a total of 100 mL of toluene
  11. dry with materialThe combined organic phases were dried over magnesium sulfate
  12. customAfter separation of the magnesium sulfate
  13. customthe solvent was removed
  14. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-1aa049de9e4b4974b44859503a993b12
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507706B2

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