AN EFFICIENT APPROACH TO BETA-OXOADIPATE DERIVATIVES AND GAMMA-OXO ACIDS BY THE REFORMATSKY REACTION OF ETHYL ALPHA-BROMOALKANOATES WITH SUCCINIC ANHYDRIDE

被引：0

作者：

SCHICK, H

LUDWIG, R

机构：

来源：

SYNTHESIS-STUTTGART | 1992年 / 04期

关键词：

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl 2-bromoalkanoates react with zinc and succinic anhydride in dimethylformamide forming 2-substituted 1-ethyl hydrogen 3-oxoadipates (hexanedioates) isolable in a yield of 56-78%. When subjected to decarboxylative saponification, they afford 4-oxoalkanoic acids in overall yields of 50-72%.

引用

页码：369 / 370

页数：2

共 18 条

[1] CONDENSATIONS .53. A REFORMATSKY TYPE CONDENSATION OF AROYL CHLORIDES WITH ETHYL ALPHA-BROMOISOBUTYRATE BY MEANS OF ZINC TO FORM BETA-KETO ESTERS
BAYLESS, PL
HAUSER, CR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (09) : 2306 - 2308
[2] FURSTNER A, 1989, SYNTHESIS-STUTTGART, P571
[3] GAUDEMAR M, 1972, ORGANOMET CHEM REV A, V8, P183
[4] STUDIES ON KETEN AND ITS DERIVATIVES .88. ETHYL 5-OXO-4-OXASPIRO[2,3]HEXANE-1-CARBOXYLATE - SYNTHESIS AND REACTIONS
KATO, T
KATAGIRI, N
SATO, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (02): : 525 - 528
[5] The effect from bromessig acid-athylester and zinc on the anhydride of the base acids
Luniak, A
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1909, 42 : 4808 - 4811
[6] MULLER A, 1931, MONATSH CHEM, V58, P24
[7] MYLARI L, 1991, J ORG CHEM, V56, P2587
[8] NUTZEL K, 1973, HOUBENWEYL, V13, P572
[9] Rathke M. W, 1975, ORG REACTIONS, V22, P423
[10] FACILE SYNTHESIS OF BETA-KETOESTERS BY A COUPLING REACTION OF THE REFORMATSKY REAGENT WITH ACYL CHLORIDES CATALYZED BY A PALLADIUM COMPLEX
SATO, T
ITOH, T
FUJISAWA, T
[J]. CHEMISTRY LETTERS, 1982, (10) : 1559 - 1560

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