Toluene → di(1H-inden-1-yl)dimethylsilane

HRID 275083

Reaction equation

HRID 275083 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]1([CH3:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:17]1[CH2:21]OCC1.[CH3:22][Si:23]([CH3:26])(Cl)Cl>CCCCCC.O>[CH3:22][Si:23]([CH3:26])([CH:21]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:16]=[CH:17]1)[CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6398DichlorodimethylsilaneHCID 7219IndeneHCID 8028Tetrahydrofuran

Product 1

HCID 599429di(1H-inden-1-yl)dimethylsilaneYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Technical-grade indene (90%) was first filtered through aluminum oxide (superactive) for crude purification and drying. 160 ml (400 mmol) of a 2.5M butylithium solution in hexane were added at room temperature to a solution of 57 ml (446 mmol) of the indene (91-92%) in a solvent mixture comprising 430 ml of toluene and 32 ml of THF, and the mixture was refluxed for 1 hour. The mixture was cooled to room temperature, and 24.2 ml (200 mmol) of dimethyldichlorosilane were added to the orange suspension. The mixture was refluxed for 5 hours and subsequently poured into water. The mixture was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate and freed from solvent under reduced pressure. The residue which remained was dried for several hours in an oil-pump vacuum at 50° C. 56 g (97%) of the ligand system 1 were obtained as a brownish oil (isomer mixture, 2 diastereomers, 1 double-bond isomer). The isomer mixture can be used directly for the preparation of the metallocene.

Workup

  1. filtrationTechnical-grade indene (90%) was first filtered through aluminum oxide (superactive) for crude
  2. custompurification
  3. customdrying
  4. temperaturethe mixture was refluxed for 1 hour
  5. temperatureThe mixture was refluxed for 5 hours
  6. extractionThe mixture was extracted several times with ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. customThe residue which remained was dried for several hours in an oil-pump vacuum at 50° C

Sources & evidence

ORD record
ord-f5c7c27cf2944810b530ef5b80a59d79
Source dataset
uspto-grants-1995_02
Patent number
US05391790

Linked notes

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