Chlorotrimethylsilane → HCID 54544702, compound

HRID 2058282Notes

Reaction equation

C[Li].C(NC(C)C)(C)C.[CH3:10][N:11]([CH3:21])[C:12](=[O:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:22][Si:23]([CH3:26])([CH3:25])Cl>C(OCC)C>[CH3:21][N:11]([C:12]([O:20][Si:23]([CH3:26])([CH3:25])[CH3:22])=[CH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:10]

Participants

Conditions

Temperature: -70 °C

Procedure

Methyllithium in diethyl ether (140 ml of 1.8 M solution, 0.25 mol) was added dropwise to a solution of 27.6 g (0.27 mol) of diisopropylamine in 40 ml of dry diethyl ether. The reaction mixture was cooled to -70° C. and a solution of 26.1 g (0.16 mol) of N,N-dimethylbenzeneacetamide in 75 ml of diethyl ether was added dropwise. The reaction mixture was warmed to 0° C. and 46 ml (0.36 mol) of trimethylchlorosilane were added dropwise. The reaction mixture was stirred at 25° C. overnight, the solid was filtered off, and the filtrate was distilled to give 7.65 g of β-(N,N-dimethylamino)-β-trimethylsiloxystyrene as a light yellow oil: bp 75°-78° C. (0.5 mm); 1H NMR (CDCl3) δ 2.18 ppm (s, 6H), 4.83 ppm (s, 1H), 6.7-7.6 ppm (m, 5H) and 0.04 ppm (s, 9H). Anal. Calcd. for C13H21NOSi: C, 66.33; H, 8.99; N, 5.95; Found: C, 66.47; H, 9.11; N, 5.78.

Workup

temperatureThe reaction mixture was warmed to 0° C.
filtrationthe solid was filtered off
distillationthe filtrate was distilled

Sources & evidence

ORD record: ord-81826be2daee465fa63aa2d95ae37134
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04215044

Reaction notes

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