Reaction Steps
1-(2-Methyl-I-tri(n-butyl)silylmethyl-2-propenyl)cyclohexanol and 1-(1-Methyl-1-(tri-n-butyl)silylmethyl-2-propenyl)cyclohexanol (92:8, 94% total yield). Major isomer: 1H NMR δ 4.85 (m, 1 H), 4.77 (d, J=1.9 Hz, 1 H), 2.12 (dd, J=8.5, 6.1 Hz, 1 H), 1.76 (d, J=0.4 Hz, 3 H), 1.68-1.10 (m, 22 H), 0.87 (t, J=7.0 Hz, 9 H), 0.76-0.70 (m, 2 H), 0.52-4.44 (m, 6 H); 13C NMR δ 147.2, 114.1, 73.2, 52.3, 35.6, 35.5, 26.9, 26.2, 25.9, 22.3, 22.2, 13.8, 12.4, 9.8; IR (neat) 3491 (br), 3068, 2954, 2924, 2870, 2856, 1637, 1456, 1375, 1196, 1082, 964, 887 cm-1 ; EIMS m/z (relative intensity) 309 ([M--C4H9 ]+ 0.5), 297 (4.3), 268 (7.8), 199 (100), 143 (67), 99 (19); HRMS calcd for C23H46OSi and C2213CH46OSi: 366.3318, 367.3347, found (EI Peak Match): 366.3301, 367.3338. Anal. Calcd: C, 75.33; H, 12.64. Found: C, 75.60; H, 12.77. Minor Isomer (difficult to isolate): 1H NMR δ 5.92 (dd, J=17.6, 10.8 Hz, 1 H), 5.11 (dd, J=10.8, 1.2 Hz, 1 H), 5.01 (dd, J=17.6, 1.2 Hz, 1 H), 1.70-1.10 (m, 22 H), 1.07 (s, 3 H), 0.88 (t, J=7.0 Hz, 9 H), 0.95-0.75 (m, 2 H), 0.53-0.45 (m, 6 H). 1-(2-(4-Methyl-3-pentenyl)-1-trimethylsilylmethyl-2-propenyl)cyclohexanol and 1-(1-Ethenyl-5-methyl-1-trimethylsilylmethyl-4-hexenyl)cyclohexanol (94:6). Major isomer: 1H NMR δ 5.17- 5.09 (m, 1 H), 4.89 (s, 1 H), 4.86 (s, 1 H), 2.20-2.00 (m, 5 H), 1.67 (s, 3 H), 1.60 (s, 3 H), 1.68-1.05 (m, 10 H), 0.84-0.69 (m, 2 H), 0.03 (s, 9 H); 13C NMR δ 151.1, 131.5, 124.4, 111.4, 73.2, 53.0, 35.6, 35.5, 25.9, 25.8, 25.7, 22.3, 22.1, 17.6, 14.9, -0.9; IR (neat) 3485 (br), 3080, 2931, 2858, 1633, 1448, 1375, 1246, 972, 891, 860, 837 cm-1 ; EIMS m/z (relative intensity) 290 ([M--H2O]+, 0.3), 275 (0.2), 210 (7), 171 (28), 141 (87), 99 (16), 73 (100); HRMS calcd for C19H36OSi and C1813CH36OSi: 308.2535, 309.2563, found (HREI Peak Match): 308.2530, 309.2559. Anal. Calcd: C, 73.96; H, 11.76. Found: C, 74.15; H, 11.80. Minor isomer: 1H NMR δ 5.81 (dd, J=17.6, 11.0 Hz, 1 H), 5.15-4.95 (m, 3 H), 2.10-0.95 (m, 14 H), 1.65 (s, 3 H), 1.59 (s, 3 H), 0.91 (d, J=15.0 Hz, 1 H), 0.75 (d, J=15.0 Hz, 1 H), 0.04 (s, 9 H); 13C NMR δ 145.5, 131.0, 125.3, 114.1, 75.8, 50.6, 33.3, 31.6, 31.5, 25.7, 24.0, 22.0, 21.8, 19.8, 17.8, 1.6; IR (neat) 3566 (br), 3080, 2933, 2858, 1631, 1450, 1375, 1259, 1246, 1155, 958, 912, 860, 845 cm-1.
