Month: February 2021

Reference of 6279-86-3, 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. 6279-86-3, name is Triethyl methanetricarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example IEthyl 2,4-dihvdroxy-7,7-dimethyl-5-oxo-5,6,7,8-tetrahvdroquinoline-3-carboxylate10 g 3-Amino-5,5-dimethyl-2-cyclohexen-1-one and 25 g 2-Ethoxycarbonyl-malonic acid diethyl ester are combined and heated for 10 minutes at 210C (bath temperature).Thereafter the mixture is cooled to room temperature and triturated with diethylether. The crystalline precipitate is collected by filtration and dried in vacuo.Yield: 9,9 g (49 % of theory)Mass spectrometry (ESI+): m/z = 280 [M+H]+ Rf-value: 0,45 (silica gel, dichloromethane/methanol 9: 1)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Triethyl methanetricarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WAGNER, Holger; BERTA, Daniela; FUCHS, Klaus; GIOVANNINI, Riccardo; HAMPRECHT, Wolfgang; KONETZKI, Ingo; STREICHER, Ruediger; TRIESELMANN, Thomas; WO2012/110599; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 34837-84-8,Some common heterocyclic compound, 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate, molecular formula is C9H9FO2, 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.

Stir at 0 C,To sodium hydride (60% in mineral oil, 2.62 g, 65.5 mmol)Anhydrous tetrahydrofuran (60 mL)Methyl 2-(4-fluorophenyl)acetate (IV-1, 5 g, 29.73 mmol) was added dropwise to the suspension.The resulting mixture was stirred at 0 C for 0.5 hours.Then slowly add methyl iodide (12.7 g, 89.4 mmol).After the addition was completed, the reaction mixture was stirred at 50 C for 5 hours.Quenched with ice water (100 mL),Extracted with ethyl acetate (40 mL ¡Á 3).Combine the organic phase,Dried over anhydrous sodium sulfate,Filter and concentrate in vacuo,Made yellow oilMethyl 2-(4-fluorophenyl)-2-methylpropanoate(IV-2, 5.7 g, yield: 98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-(4-fluorophenyl)acetate, its application will become more common.

Reference:
Patent; Guangzhou Yingsheng Biological Technology Co., Ltd.; Li Jingrong; Li Anhu; (57 pag.)CN110092804; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 24807-40-7, 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. 24807-40-7 name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, 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.

2 N Sodium hydroxide aqueous solution (3.5 mL) and water (10 mL) were added to a tetrahydrofuran-methanol solution (20 mL-10 mL) of the compound obtained in (1) (1.60 g), and stirred for 1 hour at 60C. The reaction solution was made acidic with 1 N hydrochloric acid, and then extracted with diethyl ether. The extract was washed with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from diethyl ether-hexane to obtain 3-[4-(benzyloxy)phenyl] propionic acid (1.27 g) as colorless crystals. 1H-NMR (300MHz, CDCl3); delta 2.65 (2H, t, J=7.8Hz), 2.91 (2H, t, J=7.8Hz), 5.04 (2H, s), 6.91 (2H, d, J=8.7Hz), 7.13 (2H, d, J=8.7Hz), 7.29-7.45 (5H., m)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-(4-(benzyloxy)phenyl)propanoate, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1849465; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 23877-12-5, These common heterocyclic compound, 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, 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.

Production Example 10 Synthesis of tert-Butyl 2-[2-[2-[N-2-(4-chlorophenoxy)ethylaminocarbonyl]ethyl]phenoxy]-2-methylpropionate N-(4-Chlorophenoxyethyl)-3-(2-hydroxyphenyl)propanamide (11.6 g, 36.3 mmol) was dissolved in acetonitrile (15 mL), and potassium carbonate (15.0 g, 109 mmol) was added thereto. Subsequently, tert-butyl 2-bromoisobutyrate (20.2 g, 90.7 mmol) was added thereto, followed by stirring for 4 days at 70 C. Subsequently, water was added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with brine, and the resultant mixture was subjected to drying over anhydrous sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=50/1), whereby the target compound was obtained (7.4 g, 44%).

The synthetic route of 23877-12-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOWA CO., LTD.; US2005/101636; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 105-53-3, 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 105-53-3 as follows.

Synthesis of 2-ethoxycarbonyl-malonic acid diethyl ester; Magnesium turnings (1.25 g, 50.2 mmol), dry ethanol (5 ml.) and CCI4 (0.5 ml_) were taken in a dry 100 mL of three neck flask and it was heated at 80 0C for 6 h. To this was added a mixture of diethyl malonate (8 g, 50.2 mmol) and dry ethanol (14 mL) and stirred for 2 h. The reaction EPO betamixture was cooled in a water bath when crystals were formed. After this, dry THF (20 mL) was added drop wise to dissolve the solid formed and heated for 1 h at 80 0C. To this was then added ethyl chloroformate (5 mL, 50.2 mmol) in dry THF while keeping constant boiling and the heating was further continued for 1 h followed by bringing the reaction mixture to room temperature, poured into dilute acetic acid (4 mL acetic acid in 15 mL water). This was extracted with ethyl acetate, washed with brine and the organic layers were combined and dried over anhydrous Na2SO4 and concentrated to give yellow liquid. The unreacted diethyl malonate was then removed by vacuum distillation to get the pure product as a colorless liquid. 1H NMR (300 MHz, CDCI3): 1.31 (t, 9H), 4.28 (q, 6H), 4.41 (s, 1 H). Mass: 233 (M++1).

According to the analysis of related databases, 105-53-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INDIAN INSTITUTE OF TECHNOLOGY BOMBAY; WO2006/117800; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 58656-98-7, These common heterocyclic compound, 58656-98-7, name is tert-Butyl 4-fluorobenzoate, 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.

General procedure: 3-(2,6-Dichlorophenoxy)-1H-indazole (75.0 mg; 0.27 mmol; 1.00 eq.) and tetrahydrofuran (3.00 mL) were stirred at room temperature in a round bottom flask under nitrogen atmosphere. Sodium hydride 60% in mineral oil (21.5 mg; 0.54 mmol; 2.00 eq.) was added portion wise. After 15 minutes, methyl-6-chloro-nicotinic acid (92.2 mg; 0.54 mmol; 2.00 eq.) was added and the reaction mixture was stirred at 80 C for 16 hours. The reaction mixture was cooled and diluted with ethyl acetate (50 mL). The organic layer was washed with a saturated solution of NH4Cl (20 mL) and brine (20 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue, methanol (5.00 mL) were stirred in a round bottom flask. A 10 M solution of sodium hydroxyde (1.00 mL; 10.0 mmol; 37.2 eq.) was added and the reaction mixture was stirred at 50 C for 16 hours. The reaction mixture was cooled and diluted with ethyl acetate (20 mL) and water (10 mL). The pH of the aqueous layer was adjusted to 1 using a 3 M solution of hydrochloric acid. The aqueous layer was extracted with ethyl acetate (50 mL). The organic layers were dried over MgSO4, filtered and concentrated. The residue was purified using preparative LCMS.6-(3-(2,6-Dichlorophenoxy)-1H-indazol-1-yl)nicotinic acid was isolated as a beige solid (41.0 mg; 36.6%).

The synthetic route of 58656-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ouvry, Gilles; Bouix-Peter, Claire; Ciesielski, Fabrice; Chantalat, Laurent; Christin, Olivier; Comino, Catherine; Duvert, Denis; Feret, Christophe; Harris, Craig S.; Lamy, Laurent; Luzy, Anne-Pascale; Musicki, Branislav; Orfila, Danielle; Pascau, Jonathan; Parnet, Veronique; Perrin, Agnes; Pierre, Romain; Polge, Gaelle; Raffin, Catherine; Rival, Yves; Taquet, Nathalie; Thoreau, Etienne; Hennequin, Laurent F.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5802 – 5808;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4630-80-2, name is Methyl cyclopentanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl cyclopentanecarboxylate

To a solution of diisopropylamine (56 mL, 396 mmol) in THF (85 mL) was added dropwise a solution of n-butyl lithium (240 mL, 393 mmol, 1.6M) in hexanes at -10 C while maintaining the temperature below 0 C. After addition, the solution was stirred for 30 mm at 0 C. To this, a solution of cyclopentanecarboxylic acid methyl ester (37.4 g, 263 mmol) in THF (50 mL) was added dropwise at -70 C maintaining the internal temperature between -60 to -70 C. Afteraddition, the reaction mixture was stirred for 1 h at -50 to -60 C. Then, a solution of 1,2- dibromoethane (47 mL, 545 mmol) in THF (50 mL) was added dropwise and the light brown suspension was stirred for 1 h at -70 to -60 C. Then, it was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride (200 mL) and the organic compound was extracted into ether (2X 100 mL). The combined extracts were washed with a saturated solution of sodium chloride (150 mL) and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the resulting residue was distilled at 95-105 C/2.5 mm Hg to obtain 49.6 g (80% yield) of 1-[2-bromoethyl]cyclopentanecarboxylic acid methyl ester as a colorless oil.

According to the analysis of related databases, 4630-80-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GOODNOW Jr., Robert, Alan; HAMILTON, Matthew, Michael; SIDDURI, Achyutharao; WO2013/110680; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 617-52-7, name is Dimethyl itaconate, 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 617-52-7, COA of Formula: C7H10O4

The procedure of Example D1 is repeated using 0.4 g (2.53 mmol) of dimethyl itaconate as starting material and 8.77 mg (0.0133 mmol) of compound B1 as ligand. The conversion is 100%. Removal of the solvent on a rotary evaporator gives a quantitative yield of (2R)-dimethyl succinate having an enantiomeric purity of 99.5% ee.

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; Kesselgruber, Martin; Thommen, Marc; Lotz, Mathias; US2009/270622; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 61644-18-6, 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. 61644-18-6, name is Chloromethyl isobutyrate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 8 Preparation of ((2-(((3S,7R,8R,9S)-7,8-dibenzyl-9-methyl-2-oxooxonan-3-yl)carbamoyl)-4-methoxypyridin-3-yl)oxy)methyl isobutyrate (Compound 7) To a solution of N-((3S,7R,8R,9S)-7,8-dibenzyl-9-methyl-2-oxooxonan-3-yl)-3-hydroxy-4-methoxypicolinamide (77 mg, 0.153 mmol) in acetone (3 mL) were added chloromethyl isobutyrate (31.4 mg, 0.230 mmol), NaI (4.6 mg, 0.031 mmol) and Na2CO3 (32.5 mg, 0.306 mmol), and the solution was heated to 50 C. and stirred for overnight. The solution was cooled to room temperature and concentrated, and the residue was purified by flash chromatography (SiO2, 0?100% EtOAc in hexanes) to provide the title compound (79 mg, 86%) as a colorless oil: See Table 2 for characterization data.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Chloromethyl isobutyrate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dow AgroSciences LLC; Lu, Yu; Boebel, Timothy A.; Li, Fangzheng; Bravo-Altamirano, Karla; Daeuble, SR., John F.; Yao, Chenglin; Meyer, Kevin G.; US2015/322051; (2015); 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. 3650-78-0, name is Methyl 3-(4-bromophenyl)acrylate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

820 mg (3.4 mmol) of methyl 4-bromocinnamate were dissolved in 7 ml of dry toluene, added with 116 mg (0.1 mmol) of Pd(PPh3J4, a solution of 374 mg (1.1 mmol) of 4- cyanobenzeneboronic acid in 2 ml of MeOH, 6.8 ml of 2M Na2CO3 in water, and refluxed 9 h. Addition of EtOAc, washing with water, then with brine, filtration and flash chromatography (Merck silicagel) with Hexane/EtOAc mixtures 9/1 gave 273 mg of methyl 3-(4-cyanobiphenylyl)acrylate, mp. 150-1520C.A solution of the above compound (270 mg, 1.02 mmol) and of 2-tetrahydropyranyl- O-hydroxylamine (117 mg, 1.02 mmol) in 14 ml THF was cooled at -780C, added with 1.07 ml of sodium hexamethyldisilazane, stirred 2 hrs, then heated at -2O0C, cooled again at – 780C, quenched with NH4CI, extracted with AcOEt, the extract evaporated and chromatographed (Merck silicagel) with Hexane/EtOAc 6/4 to give 189 mg of 2- EPO tetrahydropyranyloxyamide of 3-(4-cyanobiphenylyl)acrylic acid, as a white solid, mp. 211- 2130C.A solution of the above compound (187 mg, 0.54 mmol) in 5 ml of MeOH was treated with 30 mg (0.16 mmol) of p-toluenesulfonic acid, stirred 24 h at room temp, filtered and washed with MeOH, to give 96 mg of 3-(4-cyanobiphenylyl)acrylic acid hydroxyamide, mp. 212-2140C, Rf 0.3 (CH2CI2/MeOH 95/5), 1H NMR: (DMSO-d6): 6.54 (d, 1 H, -CH=, J = 15.3 Hz), 7.51 (d, 1 H, CH=, J = 15.3 Hz), 7.69 (d, 2H, 2Ar, J = 8.2 Hz), 7.82 (d, 2H, 2Ar, J = 8.2 Hz), 7.8-8.0 (m, 4H, 6Ar), 9.05 (s, 1 H, NH), 10.80 (s, 1 H, OH).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE S.P.A.; WO2007/383; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics