Chlorotrimethylsilane → 2-Methyl-2-(trimethylsilyl)propanenitrile

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Reaction Steps

2-(Trimethylsilyl)isobutyronitrile was prepared by the following procedure. To a stirred solution of 30.2 g (0.29 mole) of diisopropylamine in 220 ml of THF under argon was added at 0°-5° 184 ml of 1.58 M n-butyl lithium/hexane at a rate such that the temperature did not exceed 6°. After 15 min. 20 g (0.29 mole) of isobutyronitrile was added at 0°-5°. After 20 min., 47.3 g (0.44 mole) of chlorotrimethylsilane was added. After standing 18 h at room temperature, the mixture was filtered under argon and the filtrate was evaporated in vacuo to a solid which was extracted with ether and filtered. The filtrate was evaporated in vacuo to give 30.51 g (74%) of 2-(trimethylsilyl)isobutyronitrile as a pale yellow water-sensitive solid. Anal. Calcd. for C7H15NS: C, 59.50; H, 10.70; N, 9.92. Found: C, 59.60; H, 11.07; N, 9.74. I.R. (CCl 4): 2220 cm-1 (C≡N), 847 cm-1, 1255 cm-1 (SiMe3). NMR (90 MHz): δ0.22 (9H, SiCH3); δ1.35 (6H, CCH3).

Provenance & Evidence