A ONE-POT SYNTHESIS OF IBUPROFEN INVOLVING 3 CONSECUTIVE STEPS OF SUPERBASE METALATION

被引：25

作者：

FAIGL, F ^{[1
]}

SCHLOSSER, M ^{[1
]}

机构：

[1] UNIV LAUSANNE,INST CHIM ORGAN,RUE BARRE 2,CH-1005 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(00)92708-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot reaction sequence consisting of three consecutive metalation and electrophilic substitution stages leads to 2-(4-isobutylphenyl)propanoic acid with 52% over-all yield. A crucial step is the alkylation of deprotonated p-ethyltoluene with isopropyl bromide. In general terms, sec-alkyl halides and benzyl or allyl type alkalimetal reagents undergo coupling reactions with surprising ease.

引用

页码：3369 / 3370

页数：2

共 7 条

[1]

AMANO T, 1986, CHEM PHARM BULL, V34, P4653

[2] REACTIONS OF LITHIUM DIORGANOCUPRATES(I) WITH TOSYLATES .2. STEREOCHEMICAL, KINETIC, AND MECHANISTIC ASPECTS [J].

JOHNSON, CR ;

DUTRA, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (23) :7783-7788

[3] SELECTIVE SYNTHESIS WITH ORGANOMETALS .4. DIRECT HYDROXYLATION OF ALLYL POSITIONS [J].

RAUCHSCHWALBE, G ;

SCHLOSSER, M .

HELVETICA CHIMICA ACTA, 1975, 58 (04) :1094-1099

[4] SELECTIVE SYNTHESIS OF ORGANOMETALS .1. CONFIGURATIVE UNIFORM PRODUCT OF ALKENYL POTASSIUM INTERMEDIARY STAGES [J].

SCHLOSSER, M ;

HARTMANN, J ;

DAVID, V .

HELVETICA CHIMICA ACTA, 1974, 57 (06) :1567-1576

[5] SUPERBASES FOR ORGANIC-SYNTHESIS [J].

SCHLOSSER, M .

PURE AND APPLIED CHEMISTRY, 1988, 60 (11) :1627-1634

[6] ACTIVATION OF ORGANOLITHIUM REAGENTS [J].

SCHLOSSER, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 8 (01) :9-+

[7]

TAKAGISHI S, 1990, SYNLETT, P119

← 1 →