Dichlorodimethylsilane → (Tetramethylcyclopentadienyl)dimethylchlorosilane

HRID 369481Notes

Reaction equation

HRID 369481 reaction equation
[CH3:1][C:2]1[CH2:6][C:5]([CH3:7])=[C:4]([CH3:8])[C:3]=1[CH3:9].C([Li])CCC.[Cl:15][Si:16](Cl)([CH3:18])[CH3:17]>O1CCCC1.CCCCCC>[CH3:1][C:2]1[C:3]([CH3:9])=[C:4]([CH3:8])[C:5]([Si:16]([CH3:18])([CH3:17])[Cl:15])([CH3:7])[CH:6]=1

Participants

6

Reactant 3

HCID 6398DichlorodimethylsilaneHCID 1381631,2,3,4-TetramethylcyclopentadieneHCID 178418339Butyllithium

Product 1

HCID 131720376(Tetramethylcyclopentadienyl)dimethylchlorosilane

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a two-necked round-bottomed flask, the atmosphere in which was replaced with nitrogen, were charged 15 g of tetrahydrofuran, 12 g of n-hexane and 1.10 g of tetramethylcyclopentadiene. The mixture was cooled to 0° C. with stirring and 4.90 ml of n-butyl lithium (1.6M solution in n-hexane) (7.84 mmol as n-butyl lithium) was gradually added dropwise thereto over 20 minutes. The obtained reaction mixture in the form of a white slurry was stirred for at 0° C. for 3 hours, and a pre-cooled tetrahydrofuran (10 g) solution containing 1.01 g (7.84 mmol) of dichlorodimethylsilane was added in several divided portions. The mixture was then gradually heated to room temperature.

Workup

  1. customInto a two-necked round-bottomed flask, the atmosphere in which was replaced with nitrogen
  2. customThe obtained reaction mixture in the form of a white slurry
  3. stirringwas stirred for at 0° C. for 3 hours
  4. additionwas added
  5. temperatureThe mixture was then gradually heated to room temperature

Sources & evidence

ORD record
ord-48c8ad8012994a118792fd5630c0fe94
Source dataset
uspto-grants-2000_10
Patent number
US06136995

Reaction notes

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