Preparation of lithio ethyl acetate. Procedure for the conversion of aldehydes and ketones to .beta.-hydroxy esters

1970 ◽  
Vol 92 (10) ◽  
pp. 3222-3223 ◽  
Author(s):  
Michael W. Rathke
Keyword(s):  
Ethyl Acetate ◽  
Aldehydes And Ketones ◽  
Hydroxy Esters

Bu4N+-Controlled Addition and Olefination with Ethyl 2-(Trimethylsilyl)acetate via Silicon Activation

Synlett ◽  
2017 ◽  
Vol 28 (18) ◽  
pp. 2401-2406 ◽  
Author(s):  
Donal O’Shea ◽  
Manas Das ◽  
Atul Manvar ◽  
Ian Fox ◽  
Dilwyn Roberts
Keyword(s):  
Room Temperature ◽  
Product Formation ◽  
Unsaturated Ester ◽  
Reaction Conditions ◽  
Diverse Range ◽  
Inorganic Cation ◽  
Tetrabutyl Ammonium ◽  
Aldehydes And Ketones ◽  
Subsequent Elimination ◽  
Hydroxy Esters

Catalytic Bu4NOAc as silicon activator of ethyl 2-(trimethylsilyl)acetate, in THF, was utilized for the synthesis of β-hydroxy esters, whereas employing catalytic Bu4NOTMS gave α,β-unsaturated esters. The established reaction conditions were applicable to a diverse range of aromatic, heteroaromatic, aliphatic aldehydes and ketones. Reactions were achieved at room temperature without taking any of the specialized precautions that are in place for other organometallics. A stepwise olefination pathway via silylated β-hydroxy esters with subsequent elimination to form the α,β-unsaturated ester has been demonstrated. The key to selective product formation lies in use of the weaker acetate activator which suppresses subsequent elimination whereas stronger TMSO– activator (and base) facilitates both addition and elimination steps. The use of tetrabutyl ammonium salts for both acetate and trimethylsilyloxide activators provide enhanced silicon activation when compared to their inorganic cation counterparts.

Pinacol Coupling of Aromatic Aldehydes and Ketones in Ethyl Acetate Mediated by TiCl4‐Mg

2006 ◽  
Vol 36 (10) ◽  
pp. 1391-1399 ◽  
Author(s):  
Ke Wang ◽  
Shu‐Xiang Wang ◽  
Ming‐Zhu Gao ◽  
Ji‐Tai Li
Keyword(s):  
Ethyl Acetate ◽  
Aromatic Aldehydes ◽  
Pinacol Coupling ◽  
Aldehydes And Ketones

Pinacol Coupling of Aromatic Aldehydes and Ketones Mediated by TiCl4—Zn in Ethyl Acetate under Ultrasound.

ChemInform ◽  
2007 ◽  
Vol 38 (50) ◽  
Author(s):  
Ji-Tai Li ◽  
Xue-Li Sun ◽  
Zhi-Ping Lin ◽  
Yan-Xue Chen ◽  
Tong-Shuang Li
Keyword(s):  
Ethyl Acetate ◽  
Aromatic Aldehydes ◽  
Pinacol Coupling ◽  
Aldehydes And Ketones

Pinacol Coupling of Aromatic Aldehydes and Ketones in Ethyl Acetate Mediated by TiCl4-Mg.

ChemInform ◽  
2006 ◽  
Vol 37 (43) ◽  
Author(s):  
Ke Wang ◽  
Shu-Xiang Wang ◽  
Ming-Zhu Gao ◽  
Ji-Tai Li
Keyword(s):  
Ethyl Acetate ◽  
Aromatic Aldehydes ◽  
Pinacol Coupling ◽  
Aldehydes And Ketones

Antioxidant and anticancer activities of methanolic, ethyl acetate and chloroform extracts of Arum Palaestinum

Planta Medica ◽  
2012 ◽  
Vol 78 (11) ◽  
Author(s):  
M Diab-Assaf ◽  
RI Taleb ◽  
W Shebaby ◽  
A Mansour ◽  
CJ Moussa ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Anticancer Activities
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