211318-52-4

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 27835-00-3 ethyl (4-methylbenzoyl)acetate 
• 797756-83-3 3-hydroxy-2-(4-methylphenyl)acrylic acid ethyl ester 
• 1591911-96-4 C₂₃H₂₂FeN₂O₄ 

Relevant academic research and scientific papers

Catalytic aldol-type reaction of aldehydes with ethyl diazoacetate using quarternary ammonium hydroxide as the base

The direct aldol-type condensation of aldehydes with ethyl diazoacetate (EDA) promoted by an organic base and non-metallic catalyst such as tetrabutylammonium hydroxide (TBAOH) gave β-hydroxy-α-diazocarbonyl compounds with moderate to excellent yields. Furthermore, the reactivity and scope of various phase-transfer catalysts as well as electronically divergent aldehydes are discussed.

KF/Nano-clinoptilolite Catalyzed Aldol-Type Reaction of Aldehydes with Ethyl Diazoacetate

Abstract: Potassium fluoride supported on nano-clinoptilolite (KF/CP NPs) was used as an excellent catalytic system for direct aldol-type condensation of aldehydes with ethyl diazoacetate under solvent-less conditions. A variety of α-diazo carbonyl derivatives were prepared in good to excellent yields in short reaction times. Graphical Abstract: [Figure not available: see fulltext.]

Pyrrolidine-catalyzed condensation of ethyl diazoacetate to aldehydes in water

A simple and convenient protocol for the synthesis of-diazo carbonyl compounds from the condensation of ethyl diazoacetate to aldehydes in water was developed using pyrrolidine as a catalyst. Copyright

Synthesis of α-diazo-β-hydroxy esters using nanocrystalline MgO

Nanocrystalline magnesium oxide (NAP-MgO) has been found to be an effective heterogeneous, solid base catalyst for the direct aldol type reaction of ethyl diazoacetate and various aldehydes to afford the corresponding α-diazo-β-hydroxy esters in excellent yields with high selectivity under mild conditions.

Deep eutectic solvent (DES) as dual solvent/catalyst for synthesis of α-diazocarbonyl compounds using aldol-type coupling

Deep eutectic solvent (DES) was employed as dual solvent/catalyst in the green synthesis of α-diazocarbonyl compounds using aldol-type coupling. α-Diazocarbonyl compounds are important synthetic intermediates with useful application for synthesis of amino alcohols and acids and many natural products. Moreover, the method is environmentally friendly because of avoidance of toxic solvents or hazardous catalysts.

Safe generation and direct use of diazoesters in flow chemistry

A safe and fast method for the production of β-hydroxy-α- diazoesters in continuous flow technology is described. The synthesis involves the formation of ethyl diazoacetate in situ and the addition to several aldehydes in a two-step continuous flow microreactor setup. Rhodium acetate catalyzes a subsequent 1,2-hydride shift to give access to β-keto esters in a three-step sequence. Georg Thieme Verlag Stuttgart · New York.

Continuous flow synthesis of toxic ethyl diazoacetate for utilization in an integrated microfluidic system

An integrated microfluidic system for multiple reactions and separations of hazardous ethyl diazoacetate is presented. The integrated techniques include: a droplet technique for liquid-liquid and/or gas-liquid separation and in situ generation of the toxic reagent, a dual channel membrane technique based on a cheap polymeric microseparator for liquid-liquid separation, and a capillary microreactor for carrying out cascade reactions in a sequential and continuous manner.

Rh2(OAc)4-catalyzed 2,3-migration of β-ferrocenecarboxyl α-diazocarbonyl compounds: An efficient synthesis of ferrocene-containing α,β-unsaturated esters

A series of β-ferrocenecarboxyl α-diazocarbonyl compounds were prepared by the reaction of ferrocenoyl chloride with β-hydroxyl α-diazocarbonyl compounds in the presence of pyridine. The diazo decomposition of these ferrocene-containing diazocarbonyl compounds with Rh 2(OAc)4 resulted in 2,3-ferrocenecarboxyl migration to give ferrocene-containing α,β-unsaturated esters in high yields.

Tert-BuOK-Catalyzed condensation of ethyl diazoacetate to aldehydes and palladium-catalyzed 1,2-hydrogen migration for the synthesis of β-ketoesters under solvent-free conditions

A mild and convenient method for the condensation of ethyl diazoacetate (EDA) with aldehydes catalyzed by tert-BuOK under solvent-free conditions was developed. The corresponding α-diazo-β-hydroxy esters were further converted into β-ketoesters through palladium-catalyzed 1,2-hydrogen migration under neat conditions. The two-step transformation exemplifies a simple method for the efficient and green synthesis of β-ketoesters. The Royal Society of Chemistry 2013.

Silica-supported tetramethylguanidine: An efficient solid base for aldol-type coupling of aldehydes with ethyl diazoacetate

Silica-supported tetramethylguanidine catalyst was prepared and effectively used in the aldol-type coupling of aldehydes with ethyl diazoacetate to afford the corresponding α-diazo-β-hydroxy esters in good to excellent yields. The catalyst was quantitatively recovered from the reaction by a simple filtration and reused for a number of cycles with almost consistent activity. Georg Thieme Verlag Stuttgart.