The efficient synthesis of alkoxy-esters from hydroxy carboxylic acids using dimsyllithium in dimethylsulfoxide followed by alkylation with an alkyl halide

被引：4

作者：

Page, PCB ^{[1
]}

Chan, YH ^{[1
]}

Heaney, H ^{[1
]}

McGrath, MJ ^{[1
]}

Moreno, E ^{[1
]}

机构：

[1] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England

来源：

SYNLETT | 2004年 / 14期

关键词：

hydroxy acids; alkoxyesters; butyllithium; dimethylsulfoxide; dimsyllithium; alkyl halide;

D O I：

10.1055/s-2004-834827

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydroxy acids are converted directly into the related alkyl ether-alkyl esters in high yields in a single operation by double deprotonation using dimsyllithium in dimethylsulfoxide followed by treatment with an alkyl halide.

引用

页码：2606 / 2608

页数：3

共 45 条

[1] Simple and Convenient Synthesis of Esters from Carboxylic Acids and Alkyl Halides Using Tetrabutylammonium Fluoride
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[2] SYNTHESIS OF CARBOXYLIC-ACIDS AND THEIR METHYL-ESTERS FROM ALKYL PHENYL SULFIDES
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[3] SYNTHESIS OF ESTERS FROM SIMPLE ALKYL HALIDES AND TERTIARY AMINE SALTS OF CARBOXYLIC ACIDS
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[4] Regioselective alkylation of 5-alkyl-pyrazole-3-carboxylic esters: Application in the efficient synthesis of potent tankyrase inhibitors
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
[5] Highly efficient macrolactonization of ω-hydroxy acids using benzotriazole esters: synthesis of Sansalvamide A
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[6] DIASTEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXY CARBOXYLIC-ACIDS USING ACYLOXYSILANES
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 43 - ORGN
[7] CONVENIENT ONE POT SYNTHESIS OF ESTERS OF CARBOXYLIC-ACIDS FROM ALKYL OR ARYL HALIDES
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SIVARAM, S
SYNTHETIC COMMUNICATIONS, 1990, 20 (21) : 3273 - 3276
[8] Synthesis of F-alkyl alpha-hydroxy acids and esters from F-alkyl epoxides and F-alkyl alpha-bromo acids and esters from F-alkyl bromohydrins
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[9] The Synthesis of Long-Chain α-Alkyl-β-Hydroxy Esters Using Allylic Halides in a Frater-Seebach Alkylation
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[10] SYNTHESIS FO PRIMARY CARBOXYLIC ACIDS AND ALKYL MALONIC ACIDS FROM N-PARAFFINS BY MEANS OF TRANSMETALATION FOLLOWED BY CARBOXYLATION
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KORTE, F
MONATSHEFTE FUR CHEMIE, 1967, 98 (03): : 763 - &

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