Category: 6065-82-3

Electric Literature of 6065-82-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6065-82-3 name is Ethyl diethoxyacetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

The magnesium turnings (270 mg, 11.1 mmol) were dried in vacuo by heating with a heat gun. After cooling to room temperature and being placed under an argon atmosphere, THF (17.5 mL) was added thereto, followed by slow addition of 3-(tert-Butyldimethylsilyloxy)benzyl chloride (102) (2.57 g, 10.0 mmol) at room temperature. The reaction mixture was warmed as the result of an exothermic reaction and most of the magnesium turnings were consumed. After cooling to room temperature, it was used directly in the next reaction as a THF solution of 3-(tert-butyldimethylsilyloxy)benzylmagnesium chloride (103) was cooled to room temperature and was used as it was in the next reaction. (0404) Under an argon atmosphere, to a solution of ethyl diethoxyacetate (1.80 mL, 10.1 mmol) in THF (20 mL) was added slowly a THF solution of (103) prepared above at -78 C. After stirring at -78 C. for an hour, to this was added 20% aqueous solution of ammonium chloride (30 mL) and the product was extracted with ethyl acetate (×3). The organic layer was sequentially washed with water (×1) and saturated brine (×1), and dried over anhydrous sodium sulfate. After filtration, the mixture was concentrated under reduced pressure and the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=10/1) to give 3-[3-(tert-butyldimethylsilyloxy]phenyl]-1,1-diethoxypropan-2-one (104) as a colorless oily substance (1.90 g, 5.39 mmol, 53.9%). (0405) TLC Rf=0.48 (n-hexane/ethyl acetate=10/1); (0406) 1H NMR. (400 MHz, CDCl3) delta 0.19 (s, 6H), 0.97 (s, 9H), 1.25 (t, 6H, J=7.0 Hz), 3.54 (dq, 2H, J=9.5, 7.0 Hz), 3.69 (dq, 2H, J=9.5, 7.0 Hz), 3.82 (s, 2H), 4.63 (s, 1H), 6.68-6.75 (m, 2H), 6.81 (d, 1H, J=7.8 Hz), 7.16 (dd, 1H, J=7.8, 7.8 Hz); (0407) 13C NMR (67.8 MHz, CDCl3) delta -4.4 (2C), 15.2 (2C), 18.2, 25.7 (3C), 43.7, 63.3 (2C), 102.2, 118.5, 121.6, 122.8, 129.3, 135.2, 155.7, 202.9; (0408) IR (KBr, cm-1) 781, 839, 982, 1063, 1157, 1275, 1487, 1585, 1601, 1736, 2859, 2886, 2930, 2955, 2974; (0409) HRMS (EI) m/z 352.2073 (M, C19H32O4Si required 352.2070).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl diethoxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; JNC Corporation; Tokyo Institute of Technology; Inouye, Satoshi; Sahara, Yuiko; Iimori, Rie; Hosoya, Takamitsu; US8546568; (2013); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 6065-82-3, These common heterocyclic compound, 6065-82-3, name is Ethyl diethoxyacetate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In a 250 mL round bottom flask, 9.5 mL of n-butyl lithium (2.5 M solution in hexane, 23.8 mmol) was added via a syringe to a pre-cooled solution (-78 C.) of 2-(2-methylbut-3-yn-2-yloxy)-tetrahydro-2H-pyran 2 (4.0 g, 23.8 mmol) in 100 mL of Et2O. The resulting solution was stirred for 30 min at -78 C., then ethyl 2,2-diethoxyacetate (4.9 g, 27.7 mmol) was added with a syringe, and the stirring continued for 12 hours. The reaction mixture was poured in an ice-cold saturated aqueous solution of NH4Cl. The aqueous layer was extracted with Et2O (3*50 mL). The organic solvent was separated with a separating funnel and dried with anhydrous MgSO4. The solvent was removed under reduced pressure and the resulting pale yellow oil was purified by radial chromatography (stationary phase silica gel, hexane/AcOEt 90:10) to provide 1,1-diethoxy-5-methyl-5-(tetrahydro-2H-pyran-2-yloxy)hex-3-yn-2-one 3 as a colorless liquid. Yield: 3.2 g (10.7 mmol; 45%). 1H-NMR in CDCl3 (delta, ppm): 5.05 (1H, q, J=5.0, 3.5 Hz, THP), 4.73 (1H, s, acetal), 3.92 (1H, m, THP), 3.69 (2H, m, CH2, acetal), 3.62 (2H, m, CH2, acetal), 3.50 (1H, m, THP), 1.82 (1H, m, THP), 1.71 (1H, m, THP), 1.58 (3H, s, CH3), 1.54 (3H, s, CH3), 1.52 (4H, m, THP), 1.25 (6H, t, J=7.0 Hz, CH3, acetal). 13C-NMR in CDCl3 (delta, ppm): 182.6, 101.1, 97.87, 96.10, 81.25, 70.57, 62.95, 62.64, 62.61, 31.47, 29.45, 28.85, 25.06, 19.92, 14.90 IR (neat, cm-1): 2978, 2937, 2872, 2214, 1687, 1074. HR ESIMS+ with acetonitrile as the mobile phase, (m/z): 299.1837 (M+, C16H26O5, 299.1853), 321.1660 (m/z) ([M+Na]+, C16H26O5Na, 321.1672).

Statistics shows that Ethyl diethoxyacetate is playing an increasingly important role. we look forward to future research findings about 6065-82-3.

Reference:
Patent; DUQUESNE UNIVERSITY OF THE HOLY GHOST; US2012/245168; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 6065-82-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6065-82-3 as follows.

Under nitrogen protection, Diethoxyacetate (500 mg, 2.84 mmol) was dissolved in freshly prepared tetrahydrofuranin. When the temperature dropped to -78 C, benzylmagnesium chloride (642 mg, 4.26 mmol) was added. -78 C for 3 hours. When the reaction was warmed to room temperature, the reaction was quenched with a protected aqueous ammonium chloride solution. The organic solvent was removed by rotary evaporation and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, the organic phase was dried over anhydrous sodium sulfate, filtered,200-300 mesh silica gel column chromatography, 380mg colorless oil, yield 60%.

According to the analysis of related databases, 6065-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong University; Li Minyong; Du Lvpei; Jiang Tianyu; (37 pag.)CN105968114; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6065-82-3, name is Ethyl diethoxyacetate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6065-82-3, Product Details of 6065-82-3

Nine reactions were carried out in parallel and combined for work-up. A solution of 32 1-bromo-3,5-difluorobenzene (100 g, 518 mmol) in 15 THF (700 mL) was degassed and purged with 33 nitrogen three times. Then 2 M 34 LDA (311 mL) was added at -70 C. and the reaction mixture was stirred at -70 C. for 0.5 h under nitrogen. A solution of 35 ethyl 2,2-diethoxyacetate (96 g, 544 mmol) in THF (200 mL) was added drop-wise at -70 C. under nitrogen and the reaction mixture was stirred for 1 h. The reactions were combined and poured into ice saturated 36 ammonium chloride (10 L) in portions and extracted with EtOAc (3×3 L). The organic layer was separated, washed with brine (5 L), dried over sodium sulfate, concentrated, and purified by silica gel chromatography (eluted with petroleum ether EtOAc 1:0-100:1) to give the 37 title compound (1.26 kg, 84% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.12 (d, J=7.2 Hz, 2H), 5.15 (s, 1H), 3.61-3.7 (m, 4H), 1.2 (t, J=7.2 Hz, 6H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FATHEREE, PAUL R.; JIANG, LAN; MCKINNELL, ROBERT MURRAY; THALLADI, VENKAT R.; ZHANG, HAO; DABROS, MARTA; NZEREM, JERRY; BENJAMIN, NOAH; KLEINSCHEK, MELANIE A.; CRATER, GLENN D.; (40 pag.)US2018/311255; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6065-82-3 as follows. SDS of cas: 6065-82-3

A solution of 40 ml (224 mmol) of ethyl diethoxyacetate, 19 ml (268 mmol) of acetyl chloride and 0.1 g (0.45 mmol) of iodine is heated at 50oC for 4 hours. Only 60% of the desired product is formed. The reaction medium is cooled to room temperature, 19 ml (268 mmol) of acetyl chloride are added and the medium is heated at 50oC for a further 18 hours. The reaction medium is evaporated to dryness under vacuum. 36.3 g (100%) of crude ethyl chloroethoxyacetate are obtained.

According to the analysis of related databases, 6065-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2004/113331; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 6065-82-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6065-82-3, name is Ethyl diethoxyacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

The synthetic route of Ethyl diethoxyacetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 6065-82-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6065-82-3, name is Ethyl diethoxyacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of boron trifluoride diethyl etherate (230 mL) in chloroform (640 mL) was added propane- 1,3 -dithiol (98.3 g, 0.91 mol) dropwise at -70 C. And then to the above solution was added ethyl 2,2- diethoxyacetate (160.0 g, 0.91 mol, in chloroform (160 mL)) dropwise at 70 C over 30 min. The resulting mixture was stirred at 70 C for 30 min. The reaction mixture was quenched by the addition of water (1500 mL), and the aqueous layer was extracted with DCM. The combined organic layer was washed with saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum. The residue was purified by flash column chromatography with 0-15% ethyl acetate in petroleum ether to afford ethyl l,3-dithiane-2-carboxylate (82.6 g, 47%) as a yellow oil.

The synthetic route of Ethyl diethoxyacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6065-82-3, name is Ethyl diethoxyacetate, A new synthetic method of this compound is introduced below., name: Ethyl diethoxyacetate

General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

The synthetic route of 6065-82-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

6065-82-3, Name is Ethyl diethoxyacetate, molecular formula is C8H16O4, belongs to esters-buliding-blocks compound, is a common compound. In a patnet, author is Hatano, Manabu, once mentioned the new application about 6065-82-3, Application In Synthesis of Ethyl diethoxyacetate.

Enantioselective Aza-Friedel-Crafts Reaction of Indoles and Pyrroles Catalyzed by Chiral C-1-Symmetric Bis(phosphoric Acid)

A hydrogen bonding network in chiral Bronsted acid catalysts is important for the construction of a chiral cavity and the enhancement of catalytic activity. In this regard, we developed a highly enantioselective aza-Friedel-Crafts reaction of indoles and pyrroles with acyclic a-ketimino esters in the presence of a chiral C-1-symmetric BINOL-derived bis(phosphoric acid) catalyst. The desired alkylation products with chiral quaternary carbon centers were obtained in high yields with high enantioselectivities on up to a 1.2-g scale with 0.2 mol % catalyst loading. Interestingly, the absolute configurations of the products from indoles and pyrroles were opposite even with the use of the same chiral catalyst. Moreover, preliminary mechanistic considerations disclosed that a unique hydrogen bonding network with or without pi-pi interactions among the catalyst and substrates might partially play a pivotal role.

If you’re interested in learning more about 6065-82-3. The above is the message from the blog manager. Application In Synthesis of Ethyl diethoxyacetate.

Reference of 6065-82-3, As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. 6065-82-3, Name is Ethyl diethoxyacetate, SMILES is O=C(OCC)C(OCC)OCC, belongs to esters-buliding-blocks compound. In a article, author is Yorimitsu, Hideki, introduce new discover of the category.

Electron injection for aromatic metamorphosis of indole

Aromatic metamorphosis, endocyclic transformations of aromatic compounds, has been emerging as a new synthetic strategy in organic synthesis. This counterintuitive strategy necessitates very powerful reactions that can surmount aromaticity and the strong carbon-heteroatom bonds of the heteroaromatic rings. This Short Account describes the development of the currently most powerful elementary reaction for aromatic metamorphosis, which is electron injection from lithium metal. Exceptionally robust and aromatic N-phenylindole is subjected to the electron injection, resulting in the formation of the corresponding dianionic intermediate through reductive ring-opening. A trapping reaction of the dianionic intermediate with organoboronic acid pinacol esters provides benzazaborines, which are attractive BN-isosteres of naphthalenes. The electron injection helps establishing aromatic metamorphosis as a reliable synthetic methodology to provide novel useful molecules.

Reference of 6065-82-3, Because enzymes can increase reaction rates by enormous factors and tend to be very specific, typically producing only a single product in quantitative yield, they are the focus of active research.you can also check out more blogs about 6065-82-3.