Triethylamine → HCID 59227504, compound

Participants

Reaction Steps

4-Methylpent-4-en-2-yn-1-ol (2.0 g, 20.80 mmol), dimethylaminopyridine (0.252 g, 2.1 mmol), triethylamine (2.126 g, 21.01 mmol) and diisopropylchlorosilane (3.135 g, 20.80 mmol) were used according to the general procedure described above. The resulting clear, light yellow colored crude compound was purified by flash chromatography to yield pure product (3.914 g, 18.62 mmol, 89.5%) as clear colorless solution: Rf 0.82 (hexanes/Et2O, 9:1); 1H NMR (500 MHz, CDCl3) δ 5.28 (bs, 1H, H-5), 5.22 (bs, 1H, H-5), 4.49 (s, 1H, H-1), 4.21 (s, 1H, H-7), 1.88 (s, 3H, H-6), 0.74-1.37 (m, 14H, H-8, 9); 13C NMR (300 MHz, CDCl3) δ 126.5 (C-4), 121.8 (C-5), 86.5 (C-3), 86.3 (C-2), 54.3 (C-1), 23.2 (C-6), 17.3 (C-9), 17.2 (C-9), 12.3 (C-8); Anal. calcd for C12H22OSi: C, 68.51; H, 10.54. Found: C, 68.32; H, 10.73.

Provenance & Evidence