817-95-8

Usage

Uses

Used in Chemical Synthesis:
Ethyl ethoxyacetate is used as a chemical intermediate for the preparation of ethoxyacetylacetone. This application is crucial in the synthesis of various organic compounds and pharmaceuticals, where ethoxyacetylacetone serves as a key building block.
Used in the Preparation of Ethoxyacetylacetone:
Ethyl ethoxyacetate is utilized as a precursor in the synthesis of ethoxyacetylacetone, which is an important compound in the production of various organic and pharmaceutical products. Its role in this process highlights its value as a versatile chemical intermediate.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 260, 1943Tetrahedron, 38, p. 2733, 1982 DOI: 10.1016/0040-4020(82)80031-8

InChI:InChI=1/C6H12O3/c1-3-8-5-6(7)9-4-2/h3-5H2,1-2H3

Upstream product

• 620-73-5 phenyl chloroacetate 
• 141-52-6 sodium ethanolate 
• 64-17-5 ethanol 
• 62957-60-2 2-ethoxyacetonitrile 
• 627-03-2 3-oxapentanoic acid 
• 14077-58-8 ethoxyacetyl chloride 
• 408538-34-1 triethoxy-ethene 
• 105-39-5 chloroacetic acid ethyl ester 
• 79-11-8 chloroacetic acid 
• 58995-67-8 triethyl orthoethoxyacetate 
• 108-95-2 phenol 
• 623-73-4 diazoacetic acid ethyl ester 
• 105-57-7 diethyl acetal 
• 60-29-7 diethyl ether 

Downstream Products

• 101168-47-2 1-ethoxy-3-[2]pyridyl-acetone 
• 5452-75-5 ethyl 2-cyclohexylacetate 
• 859077-92-2 2-ethoxy-1-cyclohexyl-ethanol 
• 859777-70-1 2-ethoxy-1,1-dicyclohexyl-ethanol 
• 74-96-4 ethyl bromide 
• 623-86-9 acetoxy-acetic acid ethyl ester 
• 141-78-6 ethyl acetate 
• 105-36-2 ethyl bromoacetate 
• 102445-30-7 2-ethoxymethoxy-2-ethoxymethyl-1,3-diphenyl-propane 
• 947-91-1 Diphenylacetaldehyde 
• 93014-96-1 2-ethoxy-1,1-diphenyl-ethanol 
• 110-80-5 2-ethoxy-ethanol 
• 51770-98-0 ethoxyethylamide 
• 39242-95-0 2-ethoxyacetylhydrazine 

Relevant academic research and scientific papers

Use of α-Allyloxy-Α-trimethylsilyloxyacetate for Reductive Imino Aldol Reaction Promoted by Titanium Tetraiodide: A Rapid Access to β-Amino-α-hydroxy Esters

Under the influence of titanium tetraiodide the reductive imino aldol reaction of α-allyloxy-α-trimethylsiloxyacetate proceeded with imines to give β-amino-α-hydroxy esters in good yields.

Three-Component Reaction for the Synthesis of Highly Functionalized Propargyl Ethers

Multicomponent reactions provide efficient means to access molecular complexity. Herein, we report a copper-catalyzed three-component reaction of diazo compounds, alcohols and ethynyl benziodoxole (EBX) reagents for the synthesis of propargyl ethers. Extensive variations of the three partners of the reaction is possible, leading to highly functionalized and structurally diverse products under mild conditions. Alkynylation of a copper ylide intermediate is postulated as key step for this transformation.

Silica-supported HClO4 promotes catalytic solvent- and metal-free O-H insertion reactions with diazo compounds

Solvent-free O-H insertion reactions in the presence of diazo carbonyl compounds were carried-out in very mild conditions. Unlike the traditional metal-catalysed version, employing rhodium acetate dimer, this method uses eco-friendly silica-supported HClO4 as the catalyst. Only 0.3 mol% of this Br?nsted acid catalyst, that can also be recycled several times, is necessary to guarantee very good yields (up to 97%) in the O-H insertion reactions. Reaction set-up is simple and permitted the preparation of forty-three α-hydroxy and α-alkoxy esters/ketones in just 1 h and at room temperature.

Carbene Transfer and Carbene Insertion Reactions Catalyzed by a Mixed-Ligand Copper(I) Complex

The catalytic activity of the mixed-ligand copper(I) complex [Cu(PPh3)2(κ2-O,O"-lact)] (1) {lact = l-(+)-lactate} has been investigated in carbene transfer and carbene insertion reactions. Complex 1 catalytically promoted the diastereoselective cyclopropanation of olefins in the presence of ethyl diazoacetate (EDA), under mild conditions, and with a low catalyst loading (1 mol-%). In the case of internal alkenes, a trans/cis ratio of up to 93:7 was reached. Moreover, compound 1 easily promoted the insertion of the carbene fragment deriving from the decomposition of ethyl diazoacetate into O–H (alcohols and phenols) and N–H (amine) bonds, with formation of the corresponding ethyl 2-alkoxyacetate, ethyl 2-phenoxyacetate, and ethyl 2-aminoacetate derivatives in good to high yields.

Acetal carbonylation product preparation method

The present invention provides a method for producing an ethylene glycol production intermediate acetal carbonylation product through an acetal carbonylation reaction, wherein the method comprises that a raw material acetal and raw material gas carbon monoxide are subjected to a carbonylation reaction with a catalyst supporting an acidic EMT and FAU eutectic structure molecular sieve through a reactor to obtain the product acetal carbonylation product. According to the present invention, the conversion rate of the raw material acetal is high, the selectivity of the acetal carbonylation product is high, the service life of the catalyst is long, the additional solvent is not required, the reaction conditions are mild, the continuous production can be achieved, the industrial application potential is provided, and ethylene glycol can be produced from the obtained acetal carbonylation product sequentially through hydrogenation and hydrolysis.

Acetal carbonylation product preparation method

The present invention provides a method for producing an ethylene glycol production intermediate acetal carbonylation product through an acetal carbonylation reaction, wherein the method comprises that a raw material acetal and raw material gas carbon monoxide are subjected to a carbonylation reaction with a catalyst supporting an acidic EMT molecular sieve through a reactor to obtain the product acetal carbonylation product. According to the present invention, the conversion rate of the raw material acetal is high, the selectivity of the acetal carbonylation product is high, the service life of the catalyst is long, the additional solvent is not required, the reaction conditions are mild, the continuous production can be achieved, the industrial application potential is provided, and ethylene glycol can be produced from the obtained acetal carbonylation product sequentially through hydrogenation and hydrolysis.

PYRIDO[1,2-a]PYRIMIDONE DERIVATIVES AS A mTOR/PI3K SUPPRESSOR

The invention discloses pyrido[1,2-a]pyrimidone derivatives as a mTOR/PI3K suppressor; and in particular, this invention relates to a compound having the formula (I) structure or its pharmaceutically acceptable salts.

Isopropyl 2-ethoxyacetate—an efficient acylating agent for lipase-catalyzed kinetic resolution of amines in batch and continuous-flow modes

Productivity [conversion (c) and specific reaction rate (rbatchor rflow)] and enantiomer selectivity [enantiomeric ratio (E) and enantiomeric excess (ee) of the products] of ethyl and isopropyl esters of acetic, 2-methoxyacetic and 2-ethoxyacetic acids as acylating agents were compared in the N-acylation of (±)-1-phenylethanamine rac-1 catalyzed by variously immobilized forms of Candida antarctica lipase B (CaLB) using shake flasks and continuous-flow reactors. The effect of the temperature in the 0–80 °C range on productivity and enantiomer selectivity in KRs of rac-1 was investigated with the isopropyl esters in continuous-flow mode using CaLB-filled minireactors. Isopropyl 2-ethoxyacetate surpassed the performance of ethyl 2-methoxyacetate in terms of both productivity (1.9–2.9 times higher rate in batch mode) and enantiomeric selectivity (ee(R)-amide>99.9% compared to 99.8%) providing at 40 °C high volumetric productivity (2.22 kg L?1h?1), specific reaction rate and enantiomeric excess (rflow=783 μmol min?1g?1, ee(R)-2c>99.9%).

A stable and porous iridium(III)-porphyrin metal-organic framework: Synthesis, structure and catalysis

Self-assembly of a new metalloporphyrin tetracarboxylic ligand Ir(TCPP)Cl (TCPP = tetrakis(4-carboxyphenyl)porphyrin) with ZrCl4 in the presence of benzoic acid leads to the formation of a three-dimensional (3D) iridium(III)-porphyrin metal-organic framework (Ir-PMOF) with the formula of [(Zr6(μ3-O)8(OH)2(H2O)10)2(Ir(TCPP)Cl)3]·solvents (Ir-PMOF-1(Zr)), which possesses square-shaped channels of 1.9 × 1.9 nm2 (atom-to-atom distances across opposite Ir metal atoms) in three orthogonal directions as disclosed by the single-crystal X-ray diffraction analysis. Ir-PMOF-1(Zr) represents the first MOF bearing a self-supporting iridium-porphyrin catalytic framework, featuring high porosity and stability. The catalytic tests disclose that the activated Ir-PMOF-1(Zr) can promote O-H insertion with a turnover frequency (TOF) up to 4260 h-1. Ir-PMOF-1(Zr) can be recycled and reused for 10 runs without significant loss of catalytic activity, and the total turnover number (TON) for O-H insertion after 10 successive runs reaches 875.

A fully recyclable heterogenized Cu catalyst for the general carbene transfer reaction in batch and flow

A polystyrene-linked tris(triazolyl)methanecopper(i) cationic catalyst operates under heterogeneous conditions for the reaction of ethyl diazoacetate (EDA) with an array of substrates. Carbon-hydrogen as well as X-H (X = O, N) functionalization derived from the formal transfer of the carbene moiety (:CHCO2Et) from the copper center and subsequent insertion have been achieved, the reactions permitting repeated catalyst recycling and reuse. The addition of the same carbene unit to benzene leading to a cycloheptatriene derivative (Büchner reaction) or to phenylacetylene (cyclopropenation) took place at similar rates to the insertion processes and with the same catalyst recyclability. The use of this heterogenized cationic Cu catalyst in continuous flow has also been implemented. Key characteristics of the flow process are its high and constant turnover frequency (TOF) (residence times of 1 min still lead to full conversion in the reaction with ethanol after 48 h operation) and its suitability for the sequential performance of different types of carbene transfer reactions with a simple and affordable experimental setup.