Potassium tert-butoxide → HCID 59227484, compound

Participants

Reaction Steps

(4-Methylpent-4-en-2-ynyloxy)diisopropylsilane (1.662 g, 7.90 mmol) and KOtBu (0.092 g, 0.8199 mmol) were used according to the general procedure mentioned above. The light brown clear solution was subjected to column chromatography and yielded 8a as colorless, clear liquid (1.192 g, 5.666 mmol, 71.7%): Rf0.37 (hexanes/Et2O, 15:1); 1H NMR (500 MHz, CDCl3) δ 6.68 (t, J=1.9 Hz, 1H, H-4), 4.99 (s, 1H, H-9), 4.80 (s, 1H, H-9), 4.63 (dd, J=1.9, 0.9 Hz, 2H, H-5), 1.94 (s, 3H, H-10), 1.09-1.19 (m, 2H, H-6), 1.04 (d, J=7.3 Hz, 6H, H-7), 0.99 (d, J=7.3 Hz, 6H, H-7); 13C NMR (300 MHz, CDCl3) δ 142.4 (C-4), 142.1 (C-8), 139.8 (C-3), 116.3 (C-9), 72.7 (C-5), 20.6 (C-10), 17.3 (C-7), 17.0 (C-7), 13.3 (C-6); Anal. calcd for C12H22OSi: C, 68.51; H, 10.54. Found: C, 68.24; H, 10.61.

Provenance & Evidence