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N-((2-Trimethylsilyloxy)ethyl)aniline (Table 2,
entry 7). 1H NMR (250 MHz, CDCl3, Me4 Si): δ =
0.00 (s, 9H, Si(CH3)3)), 3.09 (t, J = 7.6 Hz, 2H), 3.64
(t, J = 7.6 Hz, 2H), 3.88 (s, 1H), 6.48–6.61 (m, 3H),
7.00–7.08 (m, 2H). 13C NMR (62.89 MHz, CDCl3,
Me4Si): δ = 0.5, 45.9, 61.0, 113.2, 117.5, 129.2, 148.3.
GCMS: m/z = 209 [M+].
4-(Trimethylsilyloxy)butan-2-one (Table 3, entry
9). IR (neat) cm−1: ν = 2958, 2898, 1715, 1358,
1250, 1169, 1097, 877, 837, 750. 1H NMR (250 MHz,
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3H, CH3CO ), 2.5 (t, J = 6.4 Hz, 2H, COCH2-),
3.7 (t, J = 6.4 Hz, 2H,
CH2O Si). 13C NMR
(62.89 MHz, CDCl3, Me4Si): δ = 0.4, 30.8, 46.5, 58.1,
207.8 (CO). GCMS: m/z = 161 [M+].
Catalyst Recovery and Reuse
The reusability of the catalyst was checked in the
multiple trimethylsilylation of benzyl alcohol with
HMDS. At the end of each reaction, the solvent was
evaporated, ether (Et2O, 10 mL) was added, and the
catalyst was filtered. The recovered catalyst was used
with fresh benzyl alcohol, HMDS, and CH2Cl2.
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ACKNOWLEDGMENT
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The author is grateful to Tabriz Petrochemical Com-
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Heteroatom Chemistry DOI 10.1002/hc