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

HRID 849908Notes

Reaction equation

[CH3:1][Si:2]([CH3:13])([CH3:12])[NH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH2:9])=[CH:6][CH:5]=1.C([Mg]Br)C.[CH3:18][Si:19](Cl)([CH3:21])[CH3:20]>O1CCCC1>[CH3:13][Si:2]([CH3:1])([CH3:12])[N:3]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH2:9])=[CH:6][CH:5]=1)[Si:19]([CH3:21])([CH3:20])[CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

4-(N-{trimethylsilyl}amino)styrene (3.5g, 18 mmol) in 20 ml tetrahydrofuran (thf) was added dropwise to ethylmagnesium bromide (1.0M/thf, 36.6 ml, 36.6 mmol). This mixture was heated at 60° C. for 6 hours then allowed to cool to room temperature. Trimethylsilyl chloride (6.35 g, 49 mmol) was added via syringe and the yellow solution heated to 60° C. for 16 hours. After removal of volatile components under reduced pressure, an off-white powder was obtained. Distillation of this at (5×10-3 mbar) yielded 4(N,N-bis {trimethylsilyl}amino) styrene as the only fraction. The colourless liquid product was stored at -30° C.

Workup

temperatureto cool to room temperature
temperaturethe yellow solution heated to 60° C. for 16 hours
customAfter removal of volatile components under reduced pressure
customan off-white powder was obtained
distillationDistillation of this at (5×10-3 mbar)

Sources & evidence

ORD record: ord-d291f0786525444583b6e8b81f7bfba8
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06015767

Reaction notes

Loading…