A short synthesis of 5-methoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoic acid methyl ester

被引：20

作者：

Henry, GE ^{[1
]}

Jacobs, H ^{[1
]}

机构：

[1] Univ W Indies, Dept Chem, Kingston 7, Jamaica

来源：

TETRAHEDRON | 2001年 / 57卷 / 25期

关键词：

alkylation; benzopyran; chromene; dealkylation; decarboxylation;

D O I：

10.1016/S0040-4020(01)00456-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Methoxy-2,2-dimethyl-2H-1-benzopyran-6-propanoic acid methyl ester was prepared in five steps and approximately 20% overall yield from 2,4-dihydroxybenzaldehyde. The two key reactions are the chromenylation between the unchelated hydroxyl group and C-3 of the resbenzaldehyde and the demethoxycarbonylation-alkylation of dimethyl malonate with a quaternary ammonium iodide. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5335 / 5338

页数：4

相关论文

共 24 条

[1] NOVEL METHODS FOR SYNTHESIS OF 2-2-DIMETHYLCHROMENS [J].

BANDARANAYAKE, WM ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (17) :970-+

[2] 3-HYDROXY-3-METHYL-1,1-DIMETHOXYBUTANE, A NEW REAGENT FOR DIMETHYL-CHROMENYLATION - SYNTHESIS OF LONCHOCARPIN, JACAREUBIN, EVODIONOL METHYL ETHER, AND OTHER CHROMENS [J].

BANDARANAYAKE, WM ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (04) :811-+

[3] FLUORINATED CHROMENES .3. SYNTHESIS OF 3-FLUORO-2,2-DIMETHYL-2H-CHROMENES [J].

CAMPS, F ;

COLL, J ;

MESSEGUER, A ;

PERICAS, MA .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (07) :1377-1379

[4] A highly efficient and practical synthesis of chromene derivatives using ring-closing olefin metathesis [J].

Chang, SB ;

Grubbs, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (03) :864-866

[5] CONVERSION OF PHENOLS INTO CHROMENS - REGIOSPECIFICITY AND SCOPE [J].

CLARKE, DG ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (09) :1007-1015

[6] REGIOSPECIFICITY OF PHENOL CHROMENYLATION [J].

CLARKE, DG ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (16) :580-582

[7]

CRUZALMANZA R, 1994, HETEROCYCLES, V37, P759

[8]

EKONG DEE, 1978, NATURE, V258, P743

[9] DESIGN, SYNTHESIS, AND TESTING OF POTENTIAL ANTISICKLING AGENTS .10. (2,2-DIMETHYLCHROMAN-6-YL)ALKANOIC ACIDS [J].

FATOPE, MO ;

ABRAHAM, DJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) :1973-1977

[10]

GABUTT CD, 1994, TETRAHEDRON, V50, P2507