Triethylamine → (3,6-Dimethylhepta-1,6-dien-4-yn-3-yloxy)diisopropylsilane

Participants

Reaction Steps

3,6-Dimethylhepta-1,6-dien-4-yn-3-ol (6d) (1.523 g, 11.18 mmol), triethylamine (1.2 g, 11.86 mmol), dimethylaminopyridine (0.153 g, 1.275 mmol) and diisopropylchlorosilane (1.657 g, 10.99 mmol) were used according to the general procedure. The brown, clear crude product was purified by column chromatography to produce the title compound (7d) as a clear colorless solution (2.641 g, 10.54 mmol, 96.3%): Rf 0.91 (hexanes/Et2O, 4:1); 1H NMR (300 MHz, CDCl3) δ 5.92 (dd, J=17.0, 10.2 Hz, 1H, H-2), 5.44 (d, J=17.0 Hz, 1H, H-1), 5.28 (bs, 1H, H-7), 5.22 (p, J=1.5 Hz, 1H, H-7), 5.07 (d, J=10.2 Hz, 1H, H-1), 4.36 (s, 1H, H-10), 1.89 (s, 3H, H-8), 1.56 (s, 3H, H-9), 0.95-1.14 (m, 14H, H-11, 12); 13C NMR (300 MHz, CDCl3) δ 142.6 (C-2), 126.4 (C-6), 121.6 (C-7), 112.8 (C-1), 89.9 (C-4), 86.9 (C-5), 70.5 (C-3), 31.6 (C-9), 23.3 (C-8), 17.6 (C-12), 17.55 (C-12), 17.53 (C-12), 12.7 (C-11), 12.6 (C-11); HRMS calcd for C15H26OSi (M+) 250.1753. found 250.1744.

Provenance & Evidence