3,5-Dimethylaniline → N-(3,5-Dimethylphenyl)-1,1-dimethyl-1-(2-methyl-4H-inden-7-yl)silanamine

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Reaction Steps

To a solution of 4.54 g (37.5 mmol) of 3,5-dimethylaniline in 110 mL of THF 15.0 mL (37.5 mmol) of 2.5 M nBuLi in hexanes was added at 0° C. This mixture was additionally stirred for 4 hours at room temperature, then cooled to −40° C., and a solution of 8.35 g (37.5 mmol) of chloro(dimethyl)(2-methyl-1H-inden-7-yl)silane in 70 mL of THF was added in one portion. The resulting mixture was stirred for 12 hours at room temperature and then evaporated to dryness. To the residue 100 mL of ether was added, and the obtained suspension was stirred for 20 minutes, and then filtered through glass frit (G3). The precipitate was additionally washed with 2×100 mL of ether. The combined filtrate was evaporated to dryness, and the residue was washed with 3×7 mL of cold hexanes and then dried in vacuum. Yield 7.26 g (63%) of white solid. 1H NMR (C6D6): δ 7.50 (dd, J=6.5 Hz, J=2.1 Hz, 1H, 6-H in indenyl), 7.24-7.30 (m, 2H, 4,5-H in indenyl), 6.35 (m, 2H, 3-H in indenyl and 4-H in 3,5-Me2C6H3), 6.27 (s, 2H, 2,6-H in 3,5-Me2C6H3), 3.27 (s, 2H, 1,1′-H in indenyl), 3.24 (s, 1H, NH), 2.08 (s, 6H, 3,5-Me in 3,5-Me2C6H3), 1.83 (s, 3H, 2-Me in indenyl), 0.45 (s, 6H, SiMe2). Anal. Calc. for C20H25NSi: C, 78.12; H, 8.19; N, 4.55%. Found: C, 78.41; H, 8.00; N, 4.38%.

Provenance & Evidence