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RSC Advances
DOI: 10.1039/C4RA04911J
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60
General procedure for trimethylsilylation of, alcohols and
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(CH2)3NHꢀSn(nꢀBu)3:
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5
To the stirred mixture of alcohol or phenol (1 mmol) and
catalyst (10 mg) in acetonitrile (1 mL), HMDS (97 mg, 0.6
mmol), were added. The reaction was then magnetically stirred at
room temperature. The progress of the reaction was monitored by
Thin Layer Chromatography (TLC). Upon completion of the
65
70
75
80
85
90
95
10 reaction, the catalyst was separated from the reaction mixture
using an external magnet, washed with acetonitrile three times to
remove all residual products then, dried for reuse in a subsequent
run. Distilled water (1 mL) was added to the filtrate and the
product was extracted with dichloromethane (2˟2 mL). The
15 organic layer was dried over anhydrous sodium sulfate (Na2SO4)
and filtered to remove any remaining residue. After the
evaporation process of the solvent, the products were purified
using a short column of silica gel eluted with ethyl acetate/ nꢀ
hexane (1:4).
20 Conclusions
In this study the prepared tributyltin catalyst was
heterogenized on magnetic nanoparticles and used as a stable and
reusable catalyst for mild and efficient trimethylsilylation of
hydroxyl groups. Primary, secondary, and tertiary alcohols and
25 phenols were efficiently converted to trimethysilyl ethers with
excellent yields and short reaction times. The advantages of this
catalyst is the ease of separation from the reaction mixture using
a permanent magnet and, its’repeated recyclability.
30. C. Nedez, A. Choplin, F. Lefebvre, J. M. Basset, E. Benazzi,
Inorg. Chem. 1994, 33, 1099.
Acknowledgement
30
We are thankful to the Tarbiat Modares University for
financial support of this work.
100 Chemistry Department, Tarbiat Modares University, P. O. Box 14155-
4838 Tehran, Iran Fax: (+98)-21-82883455; Tel: (+98)-21-82883444,
email: heydar_a@modares.ac.ir
Notes and references
35
40
45
50
55
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