Reaction of ethyl 4,4,4-trifluoroacetoacetate enolate with 3-bromo-1,1,1-trifluoroacetone: Synthesis of 2,4-bis(trifluoromethyl)furan

被引：16

作者：

Smith, JO

Mandal, BK

Filler, R

Beery, JW

机构：

[1] IIT,DEPT CHEM & BIOL SCI,CHICAGO,IL 60616

[2] SANDOZ AGRO INC,DES PLAINES,IL 60018

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1997年 / 81卷 / 02期

关键词：

ethyl-4,4,4-trifluoroacetoacetate; 3-bromo-1,1,1-trifluoroacetone; C-acylation; 2,4-bis(trifluoromethyl)furan; 2-methyl-5-trifluoromethylfuran;

D O I：

10.1016/S0022-1139(96)03518-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The potassium enolate of ethyl 4,4,4-trifluoroacetoacetate 1 reacts with 3-bromo-1,1,1-trifluoroacetone 2 in DMSO solution to yield three products. Ethyl 2,4-bis(trifluoromethyl)-4-hydroxydihydro 3 is generated via C-acylation. The hydrated trifluoromethyl ketone 4 is formed by O-alkylation and 4 reacts further with 2 to give the di-O-alkylated ketone hydrate 5. Compound 3 undergoes dehydration to the furan derivative 6 on reaction with Ac2O-ZnCl2.

引用

页码：123 / 128

页数：6

共 10 条

[1] GENERAL-METHOD FOR SYNTHESIS OF TRIFLUOROMETHYLKETONES .2. INDIRECT ALKYLATION OF ETHYL TRIFLUOROACETYLACETATE (ETFAA) [J].