Efficient method for tetrahydropyranylation/depyranylation of phenols and alcohols using a solid acid catalyst with Wells-Dawson structure

被引：55
作者：
Romanelli, GP
Baronetti, G
Thomas, HJ
Autino, JC
机构：
[1] Natl Univ La Plata, Fac Ciencias Exactas, Dept Quim, LADECOR, RA-1900 La Plata, Argentina
[2] Natl Univ La Plata, CONICET, Fac Ciencias Exactas, CINDECA,Dept Quim, RA-1900 La Plata, Argentina
[3] Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Ingn Quim, RA-1428 Buenos Aires, DF, Argentina
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 42期
关键词：
protecting group; tetrahydropyranyl; heteropolyacids; Wells-Dawson catalyst; alcohols; phenols;
D O I：
10.1016/S0040-4039(02)01822-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7589 / 7591
页数：3
相关论文
共 15 条
[1]   Heteropolyacid-based catalysis. Dawson acid for MTBE synthesis in gas phase [J].
Baronetti, G ;
Briand, L ;
Sedran, U ;
Thomas, H .
APPLIED CATALYSIS A-GENERAL, 1998, 172 (02) :265-272
[2]   PROSTAGLANDINS AND CONGENERS .20. SYNTHESIS OF PROSTAGLANDINS VIA CONJUGATE ADDITION OF LITHIUM TRANS-1-ALKENYLTRIALKYLALANATE REAGENTS - NOVEL REAGENT FOR CONJUGATE 1,4-ADDITIONS [J].
BERNADY, KF ;
FLOYD, MB ;
POLETTO, JF ;
WEISS, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09) :1438-1447
[3]  
BONGINI A, 1979, SYNTHESIS-STUTTGART, P618
[4]  
FIESER LF, 1967, REAGENTS ORGANIC SYN, V1, P256
[5]  
GREENE TW, 1991, PROTECTIVE GROUPS OR, P31
[6]   Potassium dodecatangestocobaltate trihydrate (K5CoW12O40•3H2O):: a mild and efficient catalyst for the tetrahydropyranylation of alcohols and their detetrahydropyranylation [J].
Habibi, MH ;
Tangestaninejad, S ;
Mohammadpoor-Baltork, I ;
Mirkhani, V ;
Yadollahi, B .
TETRAHEDRON LETTERS, 2001, 42 (15) :2851-2853
[7]   Solvent free tetrahydropyranylation of alcohols and phenols over sulfuric acid adsorbed on silica gel [J].
Heravi, MM ;
Ajami, D ;
Ghassemzadeh, M .
SYNTHETIC COMMUNICATIONS, 1999, 29 (06) :1013-1016
[8]   A simple and efficient hydrolyzing method for tetrahydropyranyl ethers [J].
Lee, ASY ;
Su, FY ;
Liao, YC .
TETRAHEDRON LETTERS, 1999, 40 (07) :1323-1326
[9]   Montmorillonite clays catalysis IX: A mild and efficient method for removal of tetrahydropyranyl ethers [J].
Li, TS ;
Zhang, ZH ;
Jin, TS .
SYNTHETIC COMMUNICATIONS, 1999, 29 (02) :181-188
[10]   PYRIDINIUM PARA-TOLUENESULFONATE - MILD AND EFFICIENT CATALYST FOR TETRAHYDROPYRANYLATION OF ALCOHOLS [J].
MIYASHITA, M ;
YOSHIKOSHI, A ;
GRIECO, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3772-3774
12