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

HRID 1181616

反応式

HRID 1181616 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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

後処理

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

出典と根拠

ORDレコード
ord-fac146bb6a2a488e83863c65a79b10f1
出典データセット
uspto-grants-2007_10
特許番号
US07285608B2

関連ノート

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