当前位置:首页 >> 能源/化工 >>

DIECKMANN CONDENSATION REACTION


Dieckmann Condensation reaction 2-Hydroxy-7-methoxy-5-methyl-,3,4-dihydronaphthalene-1-carboxyli c acid methyl ester

SyntheticPage 176 (2001) Submitted 28th Nov 2001, published 28th Nov 2001 lisa frost (kafs4@sussex.ac.uk), A contribution from the Caddick Group, Sussex

Chemicals Used 3-(4-methoxy-2-methoxycarbonylmethyl-6-tolyl)-propionic acid methyl ester SP:XX Lithium bis(trimethylsilyl)amide (1M in Hexane) Aldrich THF (distilled from benzophenone ketyl) Procedure To a solution of 3-(4-methoxy-2-methoxycarbonylmethyl-6-tolyl)-propionic acid methyl ester (6.32 g, 23 mmol, 1 equiv) in THF (170 mL)cooled to -78 o Cwas added LHMDS (27 mL of a 1M solution in hexanes, 27 mmol, 1.2 equiv) dropwise. The reaction was allowed to stir at this temperature for 30 minutes producing a red solution. TLC analysis [9:1; Pet:EtOAc] identified complete product formation. The reaction was quenched with NH4Cl solution (40 mL) and extracted with ethyl acetate (2 x 100 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved by chromatography on silica gel with Pet:EtOAc (9:1 v:v) to yield the title compound as a white solid (2.22 g, 40%). Author's Comments Although this reaction seems poor yielding, the conditions have been optimised for this system and this is about the best yield obtained. The reaction yield is greatly reduced if the length of reaction is increased or the temperature is altered. Further, no SM is reovered, presumably the reaction yield is low due to decomposition of the SM under the harsh base conditions. Data 1H nmr (300 MHz, CDCl3) 7.18 (1H, d, J 2.4 Hz), 6.56 (1H, d, J = 2.4

Hz), 3.92 (3H, s), 3.82 (3H, s), 2.75-2.65 (2H, m), 2.55-2.45 (2H, m), 2.30 (3H, s).

Lead Reference Rucker, Mark; Brueckner, Reinhard; Synlett.; 1997; 1187-1189


相关文章:
药物合成反应 资料_图文
Dieckmann condensation Diels–Alder reaction Eschweiler–Clarke reduction Favorskii rearrangement 与令一分子的醛或酮发生缩合,生成β -羟基醛或酮类化合物。该类 ...
100 named reaction
? http://www.organic-chemistry.org/namedreactions/darzens-reaction.shtm http://en.wikipedia.org/wiki/Darzens_condensation 32. ? ? Dieckmann Condensation ...
化学专业英语常用词3
reaction 加成反应 Electrophilic addition reaction 亲电加成反应 Nucleophilic ...condensation 克莱森缩合 Dieckmann condensation 迪克曼缩合 Perkin condensation ...
药物合成反应 人名反应_图文
Delepine 胺合成 Dieckmann condensation 醛或酮与α -卤代酸酯在碱催化下缩合...49 Reimer–Tiemann reaction Robinson annulation 罗宾逊成环反应 Rosenmund ...
Organic Chemistry Reviews-Answer(1)
Claisen ester condensation f. Dieckmann condensation g. Iodoform reaction h. Hell-Volhard-Zelinsky reaction i. Stork reaction j. Fischer esterification k. ...
有机合成习题
9、 Curtius Rearrangement 10、 Dieckmann Condensation 11、 Diels–Alder Reaction 请写出三种亲双烯体。 12、 Friedel-Crafts Acylation 为什么 Friedel-Crafts 酰...
《药物合成反应》人名反应
Dieckmann condensation 22. Favorskii rearrangement 23. Fries rearrangement 24. Gabriel synthesis 25. Gattermann–Koch reaction 26. Hofmann rearrangement 27. ...
Baeyer-Villiger_氧化
合成了 1苄基-4-哌啶酮 缩合反应 condensation (reaction) 两个或多个有机...二元羧酸酯的分子内环化反应,这时反 应又称为迪克曼反应(Dieckmann reaction)。...
化学小知识
2. 3. 4. Formation of Enolate Anions The Aldol Reaction The Claisen and Dieckmann Condensations Claisen and Aldol Condensations in the Biological world ...
北京中医药大学中 国 药 科 大 学
用反应式表示 Dieckmann Condensation(1 分) 3.写出 THF 的结构(1 分) 4.写出右侧化合物的构象式(1 分) HO OH OH 5.写出下列反应的产物及消除构象(2 分...
更多相关标签: