Remarkable effect of lithium salts in Friedel-Crafts acylation of 2-methoxynaphthalene catalyzed by metal triflates

被引：56

作者：

Kobayashi, S ^{[1
]}

Komoto, I ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(00)00610-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of a catalytic amount of a metal triflate such as Sb(OTf)(3) or Ga(OTf)(3), 2-methoxynaphthalene reacted with acetic anhydride in nitromethane-lithium perchlorate to afford 2-acetyl-6-methoxynaphthalene, a well-known intermediate for the synthesis of naproxen, in a high yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6463 / 6465

页数：3

共 27 条

[1] SHORT-STEP SYNTHESIS OF NAPROXEN - REGIOSELECTIVE FRIEDEL-CRAFTS REACTION OF 2-CHLORO-2-ALKYLTHIO-PROPIONATES [J].

ARAI, K ;

OHARA, Y ;

IIZUMI, T ;

TAKAKUWA, Y .

TETRAHEDRON LETTERS, 1983, 24 (14) :1531-1534

[2] POTENTIAL ANTIFERTILITY AGENTS .2. TETRAZOLE DERIVATIVES OF NONSTERIODAL ESTROGENS [J].

CRENSHAW, RR ;

LUKE, GM ;

BIALY, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (11) :1179-&

[3]

DAVENPORT KG, 1986, Patent No. 4593125

[4] THE FRIEDEL-CRAFTS ACETYLATION OF NAPHTHALENE IN 1,2-DICHLOROETHANE SOLUTION - KINETICS AND MECHANISM [J].

DOWDY, D ;

GORE, PH ;

WATERS, DN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (08) :1149-1159

[5] A RE-EXAMINATION OF FRIEDEL-CRAFTS ACETYLATION OF 2-METHOXYNAPHTHALENE [J].

GIRDLER, RB ;

GORE, PH ;

HOSKINS, JA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (02) :181-&

[6]

Gore P.H., 1964, FRIEDEL CRAFTS RELAT, VIII, P72

[7]

GOUDIE AC, 1978, J MED CHEM, V21, P1260, DOI 10.1021/jm00210a016

[8] DRAMATIC RATE ACCELERATIONS OF DIELS-ALDER REACTIONS IN 5-M LITHIUM PERCHLORATE DIETHYL-ETHER - THE CANTHARIDIN PROBLEM REEXAMINED [J].

GRIECO, PA ;

NUNES, JJ ;

GAUL, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4595-4596

[9] MCM-41 type molecular sieves as catalysts for the Friedel-Crafts acylation of 2-methoxynaphthalene [J].

Gunnewegh, EA ;

Gopie, SS ;

vanBekkum, H .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 106 (1-2) :151-158

[10] CATALYTIC FRIEDEL-CRAFTS ACYLATION REACTIONS USING HAFNIUM TRIFLATE AS A CATALYST IN LITHIUM PERCHLORATE-NITROMETHANE [J].

HACHIYA, I ;

MORIWAKI, M ;

KOBAYASHI, S .

TETRAHEDRON LETTERS, 1995, 36 (03) :409-412

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