Abstract:
A simple and efficient procedure to form 2-tetrahydropyranyl acetals of phenols and alcohols is reported. Wells-Dawson heteropolyacid catalyst is used both in bulk form or supported on silica, reaction conditions include room temperature and toluene as solvent. Fast deprotection of THP-acetals can be attained by mere change of the solvent using THF-1% MeOH. In both reactions the supported catalyst is easily recoverable and reusable, and the yields are good to excellent. © 2002 Elsevier Science Ltd. All rights reserved.
Registro:
| Documento: |
Artículo
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| Título: | Efficient method for tetrahydropyranylation/depyranylation of phenols and alcohols using a solid acid catalyst with Wells-Dawson structure |
| Autor: | Romanelli, G.P.; Baronetti, G.; Thomas, H.J.; Autino, J.C. |
| Filiación: | Laboratorio De Estudio De Compuestos Orgánicos (LADECOR), Departamento De Química, Universidad Nacional De La Plata, Calles 47 y 115, (1900), La Plata, Argentina
Centro De Investigación Y Desarrollo En Procesos Catalíticos (CINDECA), Departamento De Química, Universidad Nacional De La Plata-CONICET, Calle 47 No 257, (1900), La Plata, Argentina
Departamento De Ingeniería Química, Facultad De Ciencias Exactas Y Naturales, Universidad De Buenos Aires, (1428), Buenos Aires, Argentina
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| Palabras clave: | Alcohols; Heteropolyacids; Phenols; Protecting group; Tetrahydropyranyl; Wells-Dawson catalyst; acetal derivative; acid; alcohol derivative; phenol derivative; silicon dioxide; toluene; article; catalyst; chemical procedures; chemical reaction; chemical structure; depyranylation; methodology; room temperature; solid; tetrahydropyranylation |
| Año: | 2002
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| Volumen: | 43
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| Número: | 42
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| Página de inicio: | 7589
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| Página de fin: | 7591
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| DOI: |
http://dx.doi.org/10.1016/S0040-4039(02)01822-1 |
| Título revista: | Tetrahedron Letters
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| Título revista abreviado: | Tetrahedron Lett.
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| ISSN: | 00404039
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| CODEN: | TELEA
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| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v43_n42_p7589_Romanelli |
Referencias:
- Greene, T.W., Wuts, P.G.M., (1991) Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols, pp. 31-34. , Protective Groups in Organic Synthesis, 2nd Ed.; John Wiley: New York
- Li, T.-S., Zhang, Z.-H., Jin, T.-S., (1999) Synth. Commun., 29, pp. 181-188
- Arjun Reddy, M., Rajender Reddy, L., Bhanumathi, N., Rama Rao, K., (2000) Synth. Commun., 30, pp. 4323-4328
- Bernady, K.F., Brawner, M., Poletto, J.F., Weiss, M.J., (1979) J. Org. Chem., 44, p. 1438
- Miyashita, M., Yoshikoshi, A., Grieco, P.A., (1977) J. Org. Chem., 42, p. 3772
- Bongini, A., Cardillo, G., Orena, M., Sandri, S., (1979) Synthesis, p. 618
- Heravi, M.M., Ajami, D., Ghassemzadeh, M., (1999) Synth. Commun., 29, pp. 1013-1016. , and references cited therein
- Habibi, M.H., Tangestaninejad, S., Mohammadpoor-Baltork, I., Mirkhani, V., Yadollahi, B., (2001) Tetrahedron Lett., 42, pp. 2851-2853
- Romanelli, G.P., Vázquez, P., Pizzio, L., Cáceres, C.V., Blanco, M.N., Autino, J.C., Synth. Commun., , in press
- Molnár, A., Beregszászi, T., (1996) Tetrahedron Lett., 37, pp. 8597-8600
- Fieser, L.F., Fieser, M., (1967) Reagents for Organic Synthesis, 1, p. 256. , New York, NY: J. Wiley and Sons
- Lee, A.S.-Y., Su, F.-Y., Liao, Y.-Ch., (1999) Tetrahedron Lett., 40, pp. 1323-1326. , and references cited therein
- Oriyama, T., Watahiki, T., Kobayashi, Y., Hirano, H., Suzuki, T., (2001) Synth. Commun., 31, pp. 2305-2311
- Romanelli, G., Autino, J.C., Baronetti, G., Thomas, H., (2001) Molecules, 6, pp. 1006-1011
- Baronetti, G., Briand, L., Sedran, U., Thomas, H., (1998) Appl. Catal., A, 172, p. 265
Citas:
---------- APA ----------
Romanelli, G.P., Baronetti, G., Thomas, H.J. & Autino, J.C.
(2002)
. Efficient method for tetrahydropyranylation/depyranylation of phenols and alcohols using a solid acid catalyst with Wells-Dawson structure. Tetrahedron Letters, 43(42), 7589-7591.
http://dx.doi.org/10.1016/S0040-4039(02)01822-1---------- CHICAGO ----------
Romanelli, G.P., Baronetti, G., Thomas, H.J., Autino, J.C.
"Efficient method for tetrahydropyranylation/depyranylation of phenols and alcohols using a solid acid catalyst with Wells-Dawson structure"
. Tetrahedron Letters 43, no. 42
(2002) : 7589-7591.
http://dx.doi.org/10.1016/S0040-4039(02)01822-1---------- MLA ----------
Romanelli, G.P., Baronetti, G., Thomas, H.J., Autino, J.C.
"Efficient method for tetrahydropyranylation/depyranylation of phenols and alcohols using a solid acid catalyst with Wells-Dawson structure"
. Tetrahedron Letters, vol. 43, no. 42, 2002, pp. 7589-7591.
http://dx.doi.org/10.1016/S0040-4039(02)01822-1---------- VANCOUVER ----------
Romanelli, G.P., Baronetti, G., Thomas, H.J., Autino, J.C. Efficient method for tetrahydropyranylation/depyranylation of phenols and alcohols using a solid acid catalyst with Wells-Dawson structure. Tetrahedron Lett. 2002;43(42):7589-7591.
http://dx.doi.org/10.1016/S0040-4039(02)01822-1
