Compound 4d
N-(2-(tert-Butoxy)-4-methylpent-1-en-1-ylidene)-1,1,1-triisopropylsilanamine
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InChIKey XVEYYQXFZODJOM-UHFFFAOYSA-N
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following the general procedure for compound 4b, KHMDS (0.97g, 4.87 mmol, 1.2 equiv) in 4.8 mL THF and a solution of tert-butoxy nitrile 3d (0.68 g, 4.06 mmol), TIPSCl (0.96 mL, 4.46 mmol, 1.1 equiv) in 6.2 mL THF were combined to afford 1.23 g (93%) of 4d as a yellow liquid, which was used without further purification. 1H NMR: (500 MHz, CDCl3) 2.19 (d, J=7.0, 2 H, H2C(3)), 2.05-1.97 (m, J=6.6, 13.2, 1 H, HC(4)), 1.28 (s, 9 H, H3C(7)), 1.14 – 1.07 (m, 21 H, HC(8) and H3C(9)), 1.05 (d, J=6.6, 6 H, H3C(5)); 13C NMR: (125 MHz, C6D6) 208.8 (C(1)), 89.8 (C(2)), 78.9 (C(6)), 42.3 (C(3)), 28.9 (C(7)), 26.7 (C(4)), 23.0 (C(5)), 18.0 (C(9)), 12.1 (C(8)); IR: (neat) 2948 (s), 2868 (s), 2036 (s), 1656 (w), 1464 (m), 1387 (m), 1362 (m), 1279 (w), 1256 (w), 1166 (m), 1072 (w), 1016 (w), 995 (w), 921 (w), 883 (s), 824 (w), 734 (m), 683 (s); MS: (70 eV, EI) 325.2 (6.3), 300.2 (10.7), 258.1 (10.5), 242.1 (47.9), 215.1 (19.3), 242.1 (47.9), 215.1 (19.3), 200.1 (11.1), 184.1 (39.8), 157.1 (96.4), 115.1 (23.9), 103.1 (16.0), 85.1 (26.3), 73.0 (16.3), 59.0 (24.9), 57.0 (100.0); HRMS: calcd for C19H39ONSi: 325.2801, found: 325.2799.
