Chlorotrimethylsilane → Trimethyl(4-vinylphenyl)silane

HRID 1197899

Reaction equation

HRID 1197899 reaction equation
[CH3:1][Si:2]([CH3:5])([CH3:4])Cl.[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([Mg]Cl)=[CH:10][CH:9]=1)=[CH2:7].C(C1C=CC(Cl)=CC=1)=C.[Mg]>C1COCC1>[CH3:1][Si:2]([CH3:5])([CH3:4])[C:11]1[CH:12]=[CH:13][C:8]([CH:6]=[CH2:7])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 140854-ChlorostyreneHCID 5462224MagnesiumHCID 178436504HCID 178436504, compound

Product 1

HCID 595282Trimethyl(4-vinylphenyl)silaneYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

A solution of trimethylchlorosilane (7.82 g, 72.4 mmole) in dry tetrahydrofuran(THF) (40 mL) was added dropwise over a 90 minute period to a solution of (4-vinylphenyl)magnesium chloride, prepared from 4-vinylphenylchloride (10 g, 72.4 mmole) and magnesium (2.43 g, 100 mmole) in dry THF (100 mL). Temperature was maintained at 10° C. during the addition. The reaction mixture was stirred at room temperature over 20 hours under nitrogen atmosphere. The crude product was obtained by direct distillation at 45°-48° C./0.5 mm in 45% yield.

Sources & evidence

ORD record
ord-57cb22bd90c44b30bf7df4e4f4f96655
Source dataset
uspto-grants-1994_01
Patent number
US05278244

Linked notes

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