Highly efficient protection of alcohols as trityl ethers under solvent-free conditions, and recovery catalyzed by reusable nanoporous MCM-41-SO3H

被引:10
作者
Gholamzadeh, Zeynab [1 ]
Naimi-Jamal, Mohammad Reza [1 ]
Maleki, Ali [1 ]
机构
[1] Iran Univ Sci & Technol, Dept Chem, Res Lab Green Organ Synth & Polymers, Tehran 1684613114, Iran
关键词
Alcohols; Protection; Deprotection; MCM-41-SO3H nanoporous catalyst; Ball-milling; Solvent-free; NANO-ORDERED MCM-41-SO3H; STRECKER REACTION; SECONDARY; HYDROGEN; SALTS; AMINONITRILES; CONVENIENT; REAGENTS; CHLORIDE; MILD;
D O I
10.1016/j.crci.2014.01.003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient method was developed for the protection of alcohols as trityl ethers using triphenylmethanol in the presence of nanoporous MCM-41-SO3H as a heterogeneous catalyst under solvent-free ball-milling at room temperature. Low catalyst loading, high efficiency, reusability are among the advantages of this new solvent-free and environmentally friendly method. The deprotection of the produced trityl ethers was also efficiently achieved using the same catalyst in wet acetonitrile. (C) 2014 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:994 / 1001
页数:8
相关论文
共 35 条
[1]   Highly efficient and rapid synthesis of imines in the presence of nano-ordered MCM-41-SO3H heterogeneous catalyst [J].
Ali, E. ;
Naimi-Jamal, M. R. ;
Dekamin, M. G. .
SCIENTIA IRANICA, 2013, 20 (03) :592-597
[2]   Friedel-Crafts catalysts as assistants in the tritylation of less reactive hydroxyls [J].
Bernini, Roberta ;
Maltese, Maurizio .
TETRAHEDRON LETTERS, 2010, 51 (31) :4113-4116
[3]   SUBSTITUTION OF WEAKLY ACID HYDROGEN BY TRITYL CATION IN THE PRESENCE OF A HINDERED BASE [J].
BIDAN, G ;
CAUQUIS, G ;
GENIES, M .
TETRAHEDRON, 1979, 35 (02) :177-180
[4]   Protecting groups transfer: Unusual method of removal of Tr and TBDMS groups by transetherification [J].
Cabral, Nadia L. D. ;
Hoeltgebaum Thiessen, Luciano J. ;
Doboszewski, Bogdan .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2008, 27 (08) :931-948
[5]  
CHAUDHARY SK, 1979, TETRAHEDRON LETT, P95
[6]   CONVENIENT METHOD FOR THE PREPARATION OF TRITYL ETHERS FROM SECONDARY ALCOHOLS [J].
COLINMESSAGER, S ;
GIRARD, JP ;
ROSSI, JC .
TETRAHEDRON LETTERS, 1992, 33 (19) :2689-2692
[7]   Nano-ordered B-MCM-41: An efficient and recoverable solid acid catalyst for three-component Strecker reaction of carbonyl compounds, amines and TMSCN [J].
Dekamin, M. G. ;
Mokhtari, Z. ;
Karimi, Z. .
SCIENTIA IRANICA, 2011, 18 (06) :1356-1364
[8]   Zr-MCM-41 Nanoreactors as Efficient and Reusable Catalysts in the Synthesis of New Aminonitriles by the Strecker Reaction [J].
Derikvand, Zohreh ;
Derikvand, Fatemeh .
CHINESE JOURNAL OF CATALYSIS, 2011, 32 (04) :532-535
[9]   DISPROPORTIONATION OF TRITYL BENZYL ETHERS - KINETIC-ANALYSIS OF TRITYL SALT CATALYZED REACTION - EVIDENCE FOR INVOLVEMENT OF ION-PAIRS IN HYDROGEN TRANSFER STEP [J].
DOYLE, MP ;
SIEGFRIED, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (01) :163-166
[10]  
Hakimelahi G. H., 1989, J SCI IND RES IRAN, V1, P34