Chlorotrimethylsilane → N-(4-Ethenylphenyl)-1,1,1-trimethyl-N-(trimethylsilyl)silanamine

HRID 1197901Notes

Reaction equation

HRID 1197901 reaction equation
C([Mg]Br)C.[CH3:5][Si:6]([CH3:17])([CH3:16])[NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[CH2:13])=[CH:10][CH:9]=1.[CH3:18][Si:19](Cl)([CH3:21])[CH3:20]>C1COCC1>[CH3:17][Si:6]([CH3:5])([CH3:16])[N:7]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[CH2:13])=[CH:10][CH:9]=1)[Si:19]([CH3:21])([CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 19365477N-(4-Ethenylphenyl)-1,1,1-trimethylsilanamineHCID 178418443HCID 178418443, compound

Product 1

HCID 21292715N-(4-Ethenylphenyl)-1,1,1-trimethyl-N-(trimethylsilyl)silanamineYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethylmagnesium bromide in THF (0.6M, 150 mL) was added dropwise 4-[N-(trimethylsilyl)amino]styrene (8.4 g, 44 mmole) with stirring. The mixture was stirred at 40° C. for 16 hours. To the resulting solution was added trimethylsilylchloride (13 g, 120 mmole)and the mixture stirred at room temperature for 6 hours. By fractional distillation, a product was isolated at 45°-48° C./0.32 mm in 55% yield. The product was confirmed by spectral analysis to be the desired compound.

Workup

  1. stirringThe mixture was stirred at 40° C. for 16 hours
  2. stirringthe mixture stirred at room temperature for 6 hours
  3. distillationBy fractional distillation
  4. customa product was isolated at 45°-48° C./0.32 mm in 55% yield

Sources & evidence

ORD record
ord-df77590464f54e25aecb66a4ca71d461
Source dataset
uspto-grants-1994_01
Patent number
US05278244

Reaction notes

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