Potassium tert-butoxide → HCID 59227503, compound

Participants

Reaction Steps

Using (3-cyclohexenylprop-2-ynyloxy)diisopropylsilane (0.715 g, 2.854 mmol) and KOtBu (0.037 g, 0.330 mmol) produced a crude product as a colorless, clear liquid which upon flash chromatography yielded the title compound as clear colorless liquid; Rf 0.45 (hexanes/Et2O, 15:2). The isolated compound was found to have an impurity of about ˜20% with a close Rf value, hence the compound was further purified by using a chromatotron (2.0 mm silica gel) (0.537 g, 2.144 mmol, 75.1%). 1H NMR (300 MHz, CDCl3) δ 6.56 (s, 1H, H-4), 5.57 (s, 1H, H-9), 4.61 (s, 1H, H-5), 2.17-2.26 (m, 2H, H-13), 2.03-2.16 (m, 2H, H-10), 1.64-1.75 (m, 2H, H-12), 1.52-1.64 (m, 2H, H-11), 1.06-1.20 (m, 2H, H-6), 1.04 (d, J=6.6 Hz, 6H, H-7), 0.98 (d, J=6.8 Hz, 6H, H-7); 13C NMR (300 MHz, CDCl3) δ 140.3 (C-3), 138.0 (C-4), 135.7 (C-8), 128.9 (C-9), 77.8 (C-5), 26.2 (C-13), 26.0 (C-10), 22.8 (C-12), 22.4 (C-11), 17.4 (C-7), 17.1 (C-7), 13.4 (C-6); HRMS calcd for C15H27OSi (M+H)+ 251.1831. found 251.1828.

Provenance & Evidence