A NEW SYNTHESIS OF 2-ARYLOXYPROPIONIC ACIDS DERIVATIVES VIA SELECTIVE MONO-C-METHYLATION OF METHYL ARYLOXYACETATES AND ARYLOXYACETONITRILES WITH DIMETHYL CARBONATE

被引：43

作者：

BOMBEN, A ^{[1
]}

MARQUES, CA ^{[1
]}

SELVA, M ^{[1
]}

TUNDO, P ^{[1
]}

机构：

[1] UNIV VENICE,DIPARTIMENTO SCI AMBIENTALI,I-30123 VENICE,ITALY

来源：

TETRAHEDRON | 1995年 / 51卷 / 42期

关键词：

D O I：

10.1016/0040-4020(95)00718-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot procedure for the mono-C-methylation of methyl aryloxyacetates and aryloxyaceto nitriles by dimethyl carbonate (DMC) is reported The reaction is carried out in an autoclave at high temperatures (180-200 degrees C) and in the presence of a base (K2CO3 or t-BuOK). Although DMC is used either as the alkylating agent or as the solvent (30 molar excess with respect to the substrates), The selectivity towards the mono-methylated products (methyl 2-aryloxypropionates and 2-aryloxypropio nitriles, respectively) is typically up to 99%, at complete conversion; no dialkylated by-products form. The reasons of such an unusual behaviour is explained by a mechanism involving an initial carboxymethylation followed by a methylation reaction.

引用

页码：11573 / 11580

页数：8