EFFICIENT ONE-STEP CONVERSION OF TETRAHYDROPYRANYL ETHERS
395
7. Lerchen, H.G. and Kunz, H., Tetrahedron Lett., 1985,
vol. 26, p. 5257; Kunz, H. and Lerchen, H.G., Synth.
Commun., 1998, vol. 28, p. 2021.
and formates. To a solution of 1 mmol of tetra-
hydropyranyl ether and 4 ml of acylating agent we
added K5CoW12O40 ·3H2O in an amount of 0.05 mmol
for ethyl acetate, 0.01 mmol for acetic acid or ethyl
formate, or 0.02 mmol for acetic anhydride. The mix-
ture was stirred at room temperature or at the boiling
point for a time indicated in Table 1 or 2. The progress
of the reaction was monitored by GLC or TLC. The
catalyst was filtered off, the filtrate was evaporated,
20 ml of diethyl ether was added to the residue, and the
solution was washed with 5% aqueous NaHCO3 and
water, dried over Na2SO4, and evaporated. The prod-
ucts were isolated by chromatography on silica gel and
were characterized by the IR and 1H NMR spectra.
8. Saravanan, P. and Sigh, V.K., Tetrahedron Lett., 1999,
vol. 40, p. 2611.
9. Sano, T., Ohashi, K., and Oriyama, T., Synthesis, 1999,
p. 1141.
10. Chauhan, K.K., Frost, C.G., Love, I., and Waite, D.,
Synlett, 1999, p. 1743.
11. Kumar, P., Kumar Pandey, R., Bodas, M.S., and
Dongare, M.K., Synlett, 2001, p. 206; Iqbal, J. and
Srivastava, R.R., J. Org. Chem., 1992, vol. 57, p. 2001;
Orita, A., Tanahashi, C., Kakuda, A., and Otera, J.,
Angew. Chem., Int. Ed. Engl., 2000, vol. 39, p. 2877;
Yamada, S., Sugaki, T., and Matsuzaki, K., J. Org.
Chem., 1996, vol. 61, p. 5932; Chandrasekhar, S.,
Ramachander, T., and Takhi, M., Tetrahedron Lett.,
1998, vol. 39, p. 3263.
The authors are thankful to the Isfahan University
Research Council for partial support of this work.
REFERENCES
12. Hagiwara, H., Morohashi, K., Sakai, H., Suzuki, T., and
Ando, M., Tetrahedron, 1998, vol. 54, p. 5845.
1. Oriyama, T., Oda, M., Gono, J., and Koga, G., Tetra-
hedron Lett., 1994, vol. 35, p. 2027; Yang, G., Ding, X.,
and Kong, F., Tetrahedron Lett., 1997, vol. 38, p. 6725;
Oriyama, T., Kimura, M., and Koga, G., Bull. Chem. Soc.
Jpn., 1994, vol. 67, p. 885; Oriyama, T., Yatabe, K.,
Sugauttra, S., Machiguchi, Y., and Koga, G., Synlett,
1996, p. 523.
2. Greene, T.W. and Wuts, P.G.M., Protective Groups in
Organic Synthesis, New York: Wiley, 1999, 3rd ed.;
Kocienski, P.J., Protecting Groups, Stuttgart: Georg
Thieme, 1994, p. 83; Zimmermann, K., Synth. Commun.,
1995, vol. 25, p. 2959.
3. Manohar, B., Reddy, V.R., and Reddy, B.M., Synth.
Commun., 1998, vol. 28, p. 3183.
4. Takahashi, K., Shibagaki, M., and Matsushita, H., Bull.
Chem. Soc. Jpn., 1989, vol. 62, p. 2353.
5. Haslam, E., Tetrahedron, 1980, vol. 36, p. 2409 (see also
references therein).
13. Ganem, B. and Small, V.R., J. Org. Chem., 1974,
vol. 39, p. 3728.
14. Chandrasekhar, S., Ramachandar, T., Reddy, M.V., and
Takahi, M., J. Org. Chem., 2000, vol. 65, p. 4729;
Schwarz, M. and Waters, R.M., Synthesis, 1972, p. 567;
Ranu, B.C. and Hajra, A., J. Chem. Soc., Perkin
Trans. 1, 2000, p. 355; Ranu, B.C. and Hajra, A.,
J. Chem. Soc., Perkin Trans. 1, 2001, p. 2262.
15. Mohammadpoor-Baltork, I. and Khosropour, A.R.,
Monatsh. Chem., 2002, vol. 733, p. 189; Mohammad-
poor-Baltork, I. and Khosropour, A.R., Synth. Commun.,
2002, vol. 32, p. 2433.
16. Habibi, M.H., Tangestaninejad, S., Mohammadpoor-
Baltork, I., Mirkhani, V., and Yadollahi, B., Tetrahedron
Lett., 2001, vol. 42, p. 2851.
17. Habibi, M.H., Tangestaninejad, S., Mirkhani, V., and
Yadollahi, B., Tetrahedron, 2001, vol. 57, p. 8333;
Habibi, M.H., Tangestaninejad, S., Mirkhani, V., and
Yadollahi, B., Monatsh. Chem., 2001, vol. 733, p. 323.
6. Otera, J., Chem. Rev., 1993, vol. 93, p. 1449 (see also
references therein).
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 3 2005