1592
Boric Acid as Cost-Effective and Recyclable Catalyst
J. Braz. Chem. Soc.
1
1087s, 1041m, 876vs, 842vs, 747m. H NMR (CDCl3,
250 MHz) d 0.21 (s, 9 H, (CH3)3Si), 3.81 (s, 3H, CH3O),
4.66 (s, 2H, PhCH2), 6.95 (d, J 8.2 Hz, 2H, PhH), 7.32 (d,
J 8.2 Hz, 2H, PhH). 13C NMR (CDCl3, 62.9 MHz) d -0.36,
55.18, 64.38, 113.70, 128.11, 133.11, 158.86.
9. Firouzabadi, H.; Iranpoor, N.; Sobhani, S.; Gassamipour, S.;
Synthesis 2005, 595.
10. Shaterian, H. R.; Shahrekipoor, F.; Ghashang, M.; J. Mol. Catal.
A: Chem. 2007, 272, 142.
11. Khazaei, A.; Zolfigol, M. A.; Tanbakouchian, Z.; Shiri, M.;
Niknam, K.; Saien, J.; Catal. Commun. 2007, 8, 917.
12. Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.;
Mohammadpoor-Baltork, I.; Chahardahcheric, S.; Tavakoli,
Z.; J. Organomet. Chem. 2008, 693, 2041.
General procedure for deprotection of trimethylsilyl ethers
catalyzed by boric acid
Boric acid (0.0062 g, 0.1 mmol) was added to a
mixture of tms ethers (1 mmol) in H2O (2 mL) and then
the mixture was stirred at room temperature for the
specified time (see Table 4). The progress of the reaction
was monitored by TLC. On completion of the reaction, the
product was extracted with diethyl ether (3 × 10 mL) and
then the organic layer was dried over anhydrous Na2SO4.
Evaporation of the solvent under reduced pressure gave
the pure alcohols or phenols without further purification.
13. Shirini, F.; Zolfigol, M.A.;Abedini, M.; Monatsh. Chem. 2009,
140, 61.
14. Yu, Z.; Vercade, J. G.; J. Org. Chem. 2000, 65, 2065.
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Org. Lett. 2002, 4, 2141.
16. Levin, J. I.; Du, M. T.; Park. K.; Synth. Commun. 2004, 34,
2773.
17. Crouch, R. D.; Williams, A.; Synth. Commun. 2006, 36, 959.
18. Khazaei, A.; Rostami, A.; Raiatzadeh, A.; Mahboubifar, M.;
Can. J. Chem. 2007, 85, 336.
Supplementary Information
19. Lakouraj, M. M.; Akbari, A.; Indian J. Chem., Sect. B: Org.
Chem. Incl. Med. Chem. 2003, 42, 1165.
Supplementary information (FTIR and NMR spectra of
trimethyl(4-methoxybenzyloxy)silane, Figures S1-S3) is
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Acknowledgments
We are thankful to the University of Kurdistan Research
Councils for partial support of this work.
24. Kondaiah, G. C. M.; Reddy, L. A.; Babu, K. S.; Gurav, V. M.;
Huge, K. G.; Bandichhor, R.; Reddy, P. P.; Bhattacharya, A.;
Anand, R. V.; Tetrahedron Lett. 2008, 49, 106.
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Stashenko, E. E.; Synthesis 2008, 377.
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Received: May 9, 2009
Web Release Date: April 27, 2010