7
16
M. S. Reddy et al.
SHORT PAPER
Gupta, A.; Singh, R.; Singh, V. K. Synlett 1996, 69.
Oxidative Deprotection of Silyl Ethers; General Procedure
To a solution of b-CD (0.1 mmol) dissolved in distilled water (15
mL) at r.t. was added the substrate, TBDMS ether (1.0 mmol) dis-
solved in acetone (2 mL), followed by the addition of NBS (1.0
mmol). The mixture was stirred at r.t. for the specified time
(f) Vaino, A. R.; Szarek, W. A. Chem. Commun. 1996,
2351. (g) Wilson, N. S.; Keay, B. A. Tetrahedron Lett. 1997,
38, 187. (h) Farras, J.; Serra, C.; Vilarrasa, J. Tetrahedron
Lett. 1998, 39, 327. (i) Maiti, G.; Roy, S. C. Tetrahedron
Lett. 1997, 38, 495. (j) Lee, A. S. Y.; Yah, H. C.; Shie, J. J.
Tetrahedron Lett. 1998, 39, 5249. (k) Scheidt, K. A.; Chen,
H.; Follows, B. C.; Chemler, S. R.; Coffey, D. S.; Roush, W.
R. J. Org. Chem. 1998, 63, 6436. (l) Lipshutz, B. H.; Keith,
J. Tetrahedron Lett. 1998, 39, 2495. (m) Griuco, P. A.;
Markworth, C. J. Tetrahedron Lett. 1999, 40, 665.
(
Table 1). The product was extracted with EtOAc (3 × 15 mL) and
washed with brine solution (10 mL). The organic phase was dried
over anhyd Na SO and concentrated under vacuum. The crude
2
4
product thus obtained was purified by column chromatography on
silica gel (60–120 mesh) using EtOAc–hexane (1:9) as eluent.
(
1
n) Oriyana, T.; Kobayashi, Y.; Noda, K. Synlett 1998,
047. (o) Bajwa, J. S.; Vivelo, J.; Slade, J.; Repic, O.;
Acknowledgment
Blacklock, T. Tetrahedron Lett. 2000, 41, 6021. (p)Bartoli,
G.; Cupone, G.; Dalpozzo, R.; De Nino, A.; Meiuolo, L.;
Procopio, A.; Sambri, L.; Tagarelli, A. Tetrahedron Lett.
MSR and MN thank to CSIR, New Delhi, India, for financial assi-
stance.
2
002, 43, 5945.
6) (a) Olah, G.; Balaram Gupta, G. B. Synthesis 1980, 897.
b) Liu, H.-J.; Han, I.-S. Synth. Commun. 1985, 15, 759.
(
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Synthesis 2005, No. 5, 714–716 © Thieme Stuttgart · New York