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HSQC, 1H13C-HMBC, H29Si-HMBC, elemental analysis and ATR-IR. H NMR (300 MHz, C6D6, δ): 6.08
(dd, J=17.3 Hz, 10.9 Hz, 1H, H2C=CH-R), 5.26 (dd, J= 17.3 Hz, 1.6 Hz, 1H, trans-H2C=CH-R), 4.93 (dd,
10.9 Hz, 1.6 Hz, 1H, cis-H2C=CH-R), 2.07 (bs, -OH), 1.47 (s, 6H, CH3), 1.39 (s, 18H, CH3). 13C NMR (75.5
MHz, C6D6, δ): 146.7, 110.3, 74.5, 72.8, 31.4, 29.5 29Si (59.6 MHz, C6D6, δ): -91 IR (ATR, cm-1): 3399
(b), 2974 (m), 1365 (m), 1240 (m), 1182 (m), 1153 (w), 1053 (s), 1041 (s), 1011(s), 914 (m), 825 (m),
696 (s) EI-MS m/z: base peak: 261.1523 (M-15, C12H24O3SiOH: 261.1517, (Δm/z = 0.0006 amu, 2.3
ppm)); 262, (18, M-14), 261 (100, M-15), 235 (88, M-41), 205 (26, M-71), 203 (29, M-73), 179 (24, M-
97), 163 (21, M-113), 147 (52, M-129), 135 (19, M-139), 119 (16, M-157), 79 (27, M-197), 69 (22, M-
207), 57 (87, M-219) Elemental Analysis: C: 56.69% (exp.: 56.48%), H: 10.34% (exp.: 10.21%).
Synthesis of (tBuO)2(4-(CH3)C6H4O)SiOH (3d)
(tBuO)2(4-CH3C6H4O)SiCl (2d) (60 mg, 0.19 mmol) was dissolved in diethyl ether (1 mL), imidazole was
added (16 mg, 0.24 mmol) followed by deionized water (0.7 mL). The resulting mixture was stirred
for 18 hours at room temperature. The organic phase was isolated and washed 3 times with ice cold
distilled water, and dried over Na2SO4. The organic component was filtered, and solvent was
removed under reduced pressure. The yield of the product was 50 mg (0.17 mmol, 88%). The
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product, a colourless oil, was analysed by EI-MS, H NMR, C NMR, 1H13C-HSQC, 1H13C-HMBC, H29Si-
HMBC and ATR-IR. 1H NMR (300 MHz, d8-THF, δ): 7.04 (s, 2H, 3,5-positions 4-methylphenoxy), 6.93 (s,
2H, 2,6-positions 4-methylphenoxy)), 2.54 (s, 1H, OH), 2.29 (s, 3H, C-CH3 (position 4 on 4-
methylphenoxy), 1.36 (s, 18H C-CH3 (tBuO)) 13C NMR (75.5 MHz, CDCl3, δ): 151.8, 130.8, 129.8, 119.2,
74.0, 31.3, 20.6 29Si (59.6 MHz, C6D6, δ): -91 IR (ATR, cm-1): 3420 (m, broad), 2975 (m), 2931 (s), 2873
(w), 1613 (m), 1511 (s), 1473 (w), 1391 (m), 1366 (m), 1262 (m), 1245 (m), 1191 (m), 1063 (s), 1016
(m), 942 (m), 819 (s), 794 (w), 695 (m), 645 (m), 620 (w) EI-MS m/z: base peak: 298.1598 (M,
C15H26O4Si: 298.159, (Δm/z = 0.0003 amu, 1.01 ppm)); 298 (59, M), 283 (44, M-15), 228 (15, M-70),
227 (100, M-71), 186 (34, M-112), 57 (21, M-231).
Synthesis of (tBuO)2(2,4,6-(CH3)3C6H2O)SiOH (3e)
(tBuO)2(2,4,6-(CH3)3C6H2O)SiCl (2e) (400 mg, 1.16 mmol) was dissolved in diethyl ether (4 mL),
imidazole was added (91 mg, 1.34 mmol) followed by deionized water (2.7 mL). The resulting mixture
was stirred for 18 hours at room temperature. The organic phase was isolated and washed 3 times
with ice cold distilled water, and subsequently dried over Na2SO4. The organic component was
filtered, and solvent was removed under reduced pressure. The yield of the product was 214 mg
(0.65, 56%) mmol. The product, a white solid, could be used without further purification. The product
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was analysed by EI-MS, H NMR, C NMR, 1H13C-HSQC, 1H13C-HMBC, H29Si-HMBC, DEPT-45/90/135,
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elemental analysis (EA; C and H) and ATR-IR. H NMR (300 MHz, C6D6, δ): 6.79 (s 2H, 3,5 positions
2,4,6-trimethylphenoxy), 2.40 (s, 6H, C-CH3 (positions 2 & 6 on 2,4,6-trimethylphenoxy)), 2.15 (s, 3H,
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C-CH3 (position 4 on 2,4,6-trimethylphenoxy), 2.00 (s, 1H,Si-OH) 1.30 (s, 18H C-CH3 (tBuO)) C NMR
29
(75.5 MHz, C6D6, δ): 147.5, 127.8, 126.6, 126.4, 70.6, 28.00, 17.8, 15.1 Si (59.6 MHz, C6D6, δ): -93IR
(ATR, cm-1): 3334 (m, broad), 2974 (m), 2923 (w), 2869 (w), 1482 (m), 1391 (w), 1364 (m) 1313 (m),
1233 (m), 1193 (m), 1157 (w), 1044 (s), 1010 (s), 968 (m), 907 (m), 851 (m), 828 (m). 804 (w), 735 (w),
693 (s), 627 (w) EI-MS m/z: base peak: 326.1906 (M, C17H29O3SiOH: 316.1908, (Δm/z = 0.0002 amu,
0.61 ppm)); 326, (50, M), 311 (56, M-15), 255 (18, M-71), 214 (57, M-112), 213 (100, M-113), 57 (56,
M-269) Elemental analysis: C: 62.33% (exp.: 62.54%), H: 9.18% (exp.: 9.26%) Crystals suitable for X-
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