Dichlorodimethylsilane → Dimethyl(2-methylindenyl)silyl chloride

HRID 1953958Notes

Reaction equation

HRID 1953958 reaction equation
[CH3:1][Si:2]([CH3:5])(Cl)[Cl:3].O1CCCC1.[CH3:11][C:12]1[CH:13]([Li])[C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2>CCCCCC>[CH3:1][Si:2]([Cl:3])([CH3:5])[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[C:12]1[CH3:11]

Participants

5

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 8028TetrahydrofuranHCID 178506826HCID 178506826, compound

Product 1

HCID 21943870Dimethyl(2-methylindenyl)silyl chlorideYield 58%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a three-necked flask equipped with a mechanical stirrer were charged 44.5 g (345 mmol) of dimethyldichlorosilane, 300 ml of tetrahydrofuran and n-hexane, to which was added at -78° C. a 2-methylindenyllithium solution, followed by stirring at room temperature for 3 hours. After the solvent was distilled off under reduced pressure, 100 ml of hexane was added and insoluble matter was removed by centrifugation. After the solvent was distilled off under reduced pressure, distillation under reduced pressure (113° C./7mmHg) afforded 14.9 g (67 mmol, yield: 58%) of dimethyl(2-methylindenyl)silyl chloride as a pale yellow liquid.

Workup

  1. customIn a three-necked flask equipped with a mechanical stirrer
  2. distillationAfter the solvent was distilled off under reduced pressure, 100 ml of hexane
  3. additionwas added
  4. custominsoluble matter was removed by centrifugation
  5. distillationAfter the solvent was distilled off under reduced pressure, distillation under reduced pressure (113° C./7mmHg)

Sources & evidence

ORD record
ord-ae69011f711b4342ba0c54b65629a3c9
Source dataset
uspto-grants-2000_09
Patent number
US06121182

Reaction notes

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