Month: May 2021

260806-90-4, name is Methyl 3-bromo-2-methoxybenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 260806-90-4

Bis(dibenzylideneacetone)dipalladium(0) (11.5 mg, 2% mol) and 1,2,3,4,5-pentaphenyl-1-(di-tert-butylphosphino)ferrocene (29.1 mg, 1% mol) were added, under nitrogen flux, to a solution of 24 (500 mg, 2.04 mmol) in anhydrous toluene (5 ml), followed by K3PO4 (874 mg, 4.12 mmol) and n-butyl-boronic acid (251.8 mg, 2.47 mmol). The system was sealed, and the reaction mixture was stirred at 100 C for 19 h. After cooling to room temperature, toluene was removed by evaporation in vacuo to afford the crude product that was purified by flash column chromatography on silica gel (n-hexane/AcOEt 9:1) to give pure 25 (400 mg, yield: 88%). 1H NMR (200 MHz, CDCl3) delta (ppm): 0.93 (t, 3H, J = 7.3 Hz), 1.25-1.66 (m, 4H), 2.62-2.70 (m, 1H), 3.83 (s, 3H), 3.91 (s, 3H), 7.07 (t, 1H, J = 7.6 Hz), 7.35 (dd, 1H, J = 7.5 Hz, J = 1.8 Hz), 7.64 (dd, 1H, J = 7.5 Hz, J = 1.8 Hz); MS: m/z 222 (M+, 40), 223 ([M + 1]+, 100), 191 ([M – OCH3]+, 21).

The synthetic route of 260806-90-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bertini, Simone; Parkkari, Teija; Savinainen, Juha R.; Arena, Chiara; Saccomanni, Giuseppe; Saguto, Simone; Ligresti, Alessia; Allara, Marco; Bruno, Agostino; Marinelli, Luciana; Di Marzo, Vincenzo; Novellino, Ettore; Manera, Clementina; Macchia, Marco; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 526 – 536;,
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Application of 52727-57-8, A common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, molecular formula is C8H8BrNO2, 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: 1.5 equiv of PMBONH3+Cl- plus 4.5 equiv of LiHMDS (at 0 C for 2 h) or 4.1 equiv of LDA (from -78 C to -10 C, 0.5 h); yields were similar.

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:
Article; Bosch, Lluis; Mouscadet, Jean-Franois; Ni, Xio-Ju; Vilarrasa, Jaume; Tetrahedron Letters; vol. 52; 7; (2011); p. 753 – 756;,
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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. 36692-49-6, name is Methyl 3,4-diaminobenzoate, A new synthetic method of this compound is introduced below., Product Details of 36692-49-6

General procedure: Substituted 1,2-phenylenediamines (1 mmol) and substituted phenacyl bromides (1 mmol) were dissolved in acetonitrile (5 ml). To this solution, K10-Mont. clay (50 mg) was added and heated at 50 C for 3 h. After completion, the reaction mixture was filtered to remove the catalyst and washed with ethyl acetate (10 mL). The filtrate was concentrated and the residue was purified by column chromatography using hexane:ethyl acetate (15 % ethyl acetate in hexane) as an eluent to afford quinoxaline derivatives in high yields. The recovered catalyst was thoroughly washed with ethyl acetate, air dried, activated at 80 C for 3 h and reused for successive runs. The purified products are characterized by their 1H, 13C NMR as well as by mass spectral data

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:
Article; Jeganathan, Mariappan; Dhakshinamoorthy, Amarajothi; Pitchumani, Kasi; Tetrahedron Letters; vol. 55; 9; (2014); p. 1616 – 1620;,
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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. 55954-23-9, name is Methyl 2,4-dichlorophenylacetate, A new synthetic method of this compound is introduced below., COA of Formula: C9H8Cl2O2

To a suspension of 2,4-dichlorophenylacetic acid methyl ester (1 .38 mmol) and paraformaldehyde (1 .45 mmol) in 2.7 mL DMSO was added NaHC03 (0.07 mmol). The reaction mixture was stirred at RT for 2 h and then quenched with water. The mixture was neutralized with 1 M HCI solution and extracted with EtOAc (2x). The combined organic layers were dried over MgS04 and concentrated in vacuo. Purification by CC (KP-SIL from Biotage) using Hept to Hept/EtOAc (1/1 ) gives the desired compound as colorless oil; LC-MS (B): tR = 0.77 min; 1 H NMR ((CD3)2SO) delta: 7.64 (d, 1 H), 7.46 (m, 2H), 5.14 (t, 1 H), 4.18 (m, 1 H), 3.92 (m, 1 H), 3.72 (m, 1 H), 3.62 (s, 3H).

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; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; KIMMERLIN, Thierry; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; WO2013/14587; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35179-98-7, name is Chloromethyl ethyl carbonate, 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 35179-98-7, SDS of cas: 35179-98-7

Compound 7 (500 mg, 0.83 mmol), compound 11 (571.9 mg, 4.14 mmol), potassium carbonate (572.7 mg, 4.14 mmol) and potassium iodide (68.1 mg, 0.41 mmol) were added to the reaction flask, and 10 ml of DMF was added and heated to 60 C reactionThe reaction was completed by TLC, and the temperature was lowered to room temperature, diluted with excess water, extracted with ethyl acetate for 3-4 times, and the organic phases were combined and saturated.Wash with salt water, concentrate,Purification by silica gel column chromatography gave 99 mg of product.Yield: 16.9%.

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; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Zhao Jiuyang; (54 pag.)CN109320553; (2019); A;,
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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. 42726-73-8, name is tert-Butyl methyl malonate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl methyl malonate

Sodium hydride (3.04 g of a 50percent oil dispersion, 127 mmol) is suspended in dimethylformamide (300 ml) and the suspension is cooled to 0° C. t-Butyl methyl malonate (20.08 g, 115 mmol) is added dropwise slowly and the reaction mixture is warmed to room temperature. 1,7-Dibromoheptane (29.75 g, 115 mmol) is added dropwise and the mixture is stirred for 3 hours. The mixture is partitioned between diethyl ether (500 ml) and water (1000 ml). The organic layer is washed with water (3*500 ml), brine (1*500 ml), dried (MgSO4) and the solvent is evaporated. The product is purified by silica gel chromatography (10percent ethyl acetate/hexane) to give t-butyl methyl 7-bromoheptylmalonate as an oil.

According to the analysis of related databases, 42726-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ciba-Geigy Corporation; US5244889; (1993); A;,
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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 2435-36-1 as follows. Recommanded Product: Dimethyl cyclopentane-1,3-dicarboxylate

Diisopropylamine (210.0g, 201.0mmol), tetrahydrofuran (5.0L) was added to a 10L four-necked flask with mechanical stirring and thermometer. 80.0ml / 2.5M, 200.0mmol), keep -10 -60 and stir for 15min, add hexamethylphosphonic acid triamine (370.0g, 207.0mmol), control temperature -10 -60 , add cyclopentane dropwise -1,3-Dicarboxylic acid methyl ester (150.0g, 80.6mmol), after incubation and stirring for half an hour, dropwise add diiodomethane (210.0g, 80.6mmol), return to room temperature for 20min, dropwise add acetic acid (50ml) to quench After the reaction, 2.0L of 2N hydrochloric acid was added, the liquid was stirred and separated, and the organic phase was collected and concentrated to obtain the crude product, which was distilled under reduced pressure with an oil pump. Fractions around 100 C to 105 C were collected to obtain 95.0g of dicyclohexane [2.1.1] hexane- Dimethyl 1,4-dicarboxylate is a light yellow liquid with a purity of 98% and a yield of 59%.

According to the analysis of related databases, 2435-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Suzhou Laikeshide Pharmaceutical Co., Ltd.; Zhou Miao; Yu Jurong; (5 pag.)CN110878019; (2020); A;,
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Reference of 4630-80-2, 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. 4630-80-2 name is Methyl cyclopentanecarboxylate, 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.

n-Butyllithium (2.5 M in hexanes) (1.24 ml, 3.09 mmol) was addeddropwise to a -78 oc solution of diisopropylamine (0.440 ml, 3.09 mmol) in tetrahydrofuran(THF) (13 ml). The mixture was allowed to warm to room temperature and stirred for 15minutes. The mixture was cooled to -78 oc before methyl cyclopentanecarboxylate (0.355ml, 2.81 mmol) was added dropwise. The mixture was warmed to 0 oc and stirred for 30minutes before being cooled again to -78 C. A solution of 2-(benzyloxy)-4-(bromomethyl)-1-methoxybenzene (1.035 g, 3.37 mmol) in tetrahydrofuran (THF) (5 ml) was addeddropwise. The mixture was stirred an additional 15 minutes at -78 oc and then allowed towarm to room temperature and stirred overnight. The mixture was diluted with ethylacetate, washed with saturated ammonium chloride, washed with brine, and concentrated.The residue was purified by medium pressure reverse phase chromatography (C18 Iacetonitrile I water I 0.1% formic acid I 10% to 100% gradient). Fractions wereconcentrated. The residue was dissolved in acetonitrile and the mixture concentrated in order to azeotrope remaining water. Drying under vacuum gave methyl 1-(3-(benzyloxy)-4-methoxybenzyl)cyclopentane-1-carboxylate (716 mg, 2.02 mmol, 72 % yield) as a clear oil.LCMS (ESI) mlz: 377.3 (M+Nat.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; DICKSON, Hamilton D.; KAZMIERSKI, Wieslaw Mieczyslaw; LEIVERS, Martin R.; WEATHERHEAD, John Gordon; (389 pag.)WO2018/154466; (2018); A1;,
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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. 103-25-3, name is Methyl 3-phenylpropionate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H12O2

Several other esters, whose structure and names are described in Table 3, were hydro genated under the conditions described above using preformed RuCl2(L-I). Isolated yield are given in Table 4.Table 3: Structure and names of substrates usedTable 4: Hydrogenation of esters using RuCl2(L-I) EPO Sub.: Substrate as described in Table 3.Conv.: Conversion (in %, analysed by GC after silylation) of ester to alcohol after 2h30min.Reaction conditions: Substrate (20 mmol), H2 gas (50 bars), RuCl2(L-I) 0.05 mol%,NaOMe 10 mol%, THF (14 mL) at 1000C during 2h 30min.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 103-25-3.

Reference:
Patent; FIRMENICH SA; WO2006/106484; (2006); A1;,
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Electric Literature of 87661-20-9, The chemical industry reduces the impact on the environment during synthesis 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, I believe this compound will play a more active role in future production and life.

tert-Butyl 1-allylcyclopropanecarboxylate STR11 A solution of 34.1 g (0.24 mol) of tert-butyl cyclopropanecarboxylate in 25 ml of tetrahydrofuran was added dropwise at -70 C. to a mixture of 33.6 ml (0.24 mol) of diisopropylamine, 150 ml of a 1.5 molar solution of n-butyllithium in n-hexane (=0.24 mol of butyllithium) and 100 ml of tetrahydrofuran. Stirring was carried out for 3 hours at -70 C., after which a solution of 27.8 g (0.23 mol) of allyl bromide in 25 ml of tetrahydrofuran was added dropwise. Thereafter, the reaction mixture was stirred for a further 2 hours at -70 C. and then for 12 hours at 20 C. After hydrolysis with 50 ml of saturated aqueous ammonium chloride solution and after phase separation, the organic phase was worked up in a conventional manner to obtain the product. The crude product was purified by distillation. Yield: 61%, bp.: 86-88 C. at 30 mbar; colorless oil.

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, tert-Butyl cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF Aktiengesellschaft; US5371268; (1994); A;,
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