TRIMETHYLSILYLATION OF ALCOHOLS AND PHENOLS
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General Procedure for Trimethylsilylation of Alcohols and Phenols
A mixture of alcohol or phenol (1 mmol), MTSA (0.03 mmol), and HMDS (1
mmol) was prepared and stirred at room temperature for appropriate time (Table 3). After
completion of the reaction (TLC), 10-mL water was added and the mixture was extracted
with diethyl ether (3 × 10 mL). The organic layer was separated, dried (MgSO4), and
filtered. Evaporation of the solvent under reduced pressure gave the highly pure product
without further purification. The desired pure products were characterized by comparison
of their NMR data with those of known compounds. The spectral data of some new
trimethylsilylethers are given below.
1
(1-(3-Bromophenyl)ethoxy)trimethylsilane (2i). H NMR (400 MHz,
CDCl3): δ 7.40–7.31 (m, 4H), 4.82 (q, J = 8.4, 1H), 1.49 (d, J = 4.4, 3H), 0.15 (s, 9H);
13C NMR (100 MHz, CDCl3): δ 149.3, 135.1, 130.2, 127.4, 125.8, 124.2, 68.9, 26.9, 0.08;
Anal. Calcd. for C11H17BrSi: C 48.35, H 6.27; found: C 48.28, H 6.35.
(4-chlorocyclohexa-2,4-dienyl)(4-chlorophenyl)methoxy)trimethylsilane
1
(2j). H NMR (400 MHz, CDCl3): δ 7.60–7.53 (m, 4H), 7.28–7.20 (m, 4H), 5.89 (s, 1H),
0.28 (s, 9H); 13C NMR (100 MHz, CDCl3): δ 164.8, 158.2, 141.2, 140.2, 116.3, 115.0,
76.2, 0.10; Anal. Calcd. for C16H18Cl2OSi: C 59.07, H 5.58; found: C 59.01, H 5.63.
1
(4-(4-methoxyphenyl)butoxy)trimethylsilane (2o). H NMR (400 MHz,
CDCl3): δ 7.10 (d, J = 8.4, 2H), 6.82 (d, J = 8.4, 2H), 3.72 (s, 3H), 3.70–3.67 (m, 2H),
2.58–2.54 (m, 2H), 1.65–1.60 (m, 2H), 1.47–1.40 (m, 2H), 0.19 (s, 9H); 13C NMR (100
MHz, CDCl3): δ 158.2, 132.1, 130.4, 114.2, 65.2, 55.9, 36.8, 33.1, 26.9, 0.12; Anal. Calcd.
for C14H24O2Si: C 66.61, H 9.58; found: C 66.72, H 9.48.
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