Tag: M.W=100-200

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. 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate

Preparation of intermediate 5B:l-(((5-bromopyrimidin-2-yl)oxy)methyl)cyclopropane carboxylic acid ethyl ester5-Bromo-2-hydroxypyrimidine (850 mg, 4.86 mmol) and triphenylphosphine (1.91 g, 7.3 mmol) were dissolved in THF, to which was added diisopropyl azodicarboxylate DIAL) (1.19 mL, 6 mmol). The reaction solution was stirred at room temperature for 1 h, after which was added l-(hydroxymethyl)cyclopropanecarboxylic acid ethyl ester 5A (700 mg, 4.86 mmol). The reaction proceeded overnight at room temperature under stirring. The solvents were evaporated and the residue was purified with a silica gel column (n-hexane: ethyl acetate = 20: 1) to give 580 mg of white solid 5B. Yield: 39.7%.MS (ESI, m/z): [M+H]+: 300.9; 1H-NMR (300 MHz, CDC13): 8.55 (s, 2H), 4.53 (s, 2H), 4.16 (q, 2H, J= 7.2 Hz), 1.41(dd, 2H, J = 4.2 Hz, J = 3.0 Hz), 1.23 (t, 3H, J= 7.2 Hz), 1.06 (dd, 2H, J = 4.2 Hz, J= 3.0 Hz).

According to the analysis of related databases, 3697-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIJING HANMI PHARMACEUTICAL CO., LTD; ZHANG, Bo; YANG, Jun; LIU, Jinming; HUANG, Hai; WU, Yong; TAO, Ran; XU, Jiangcheng; SHEN, Ning; MOON, Sunghwan; KIM, Maengsup; WO2013/56679; (2013); A1;,
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Application of 31930-34-4, 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. 31930-34-4 name is Ethyl cis-3-Bromoacrylate, 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.

General procedure: A dry and argon-flushed 10 mL Schlenk-tube, equipped with a stirring bar and a septum, was charged with dryCoCl2 (6.5 mg, 0.05 mmol, 5 mol%) and dry THF (2.0 mL). The respective aryl halide (1.0 mmol, 1.0 equiv) wasadded at room temperature. Then, a solution of the appropriate (hetero)aryl zinc pivalate (1.5 mmol, 1.5 equiv)was added dropwise over 5 min via syringe. The reaction was stirred at 40 C and monitored by GC-analysis(C11H24 was used as an internal standard). Upon consumption of the starting material, saturated aqueous NH4Clsolution (5 mL) and ethyl acetate (5 mL) were added, the phases were separated and the aqueous phase was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with aqueous NaOHsolution (2 M, 50 mL) and dried over Na2SO4. The solvents were evaporated and the residue was subjected tocolumn chromatography purification on silica yielding the respective title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl cis-3-Bromoacrylate, and friends who are interested can also refer to it.

Reference:
Article; Hofmayer, Maximilian S.; Hammann, Jeffrey M.; Lutter, Ferdinand H.; Knochel, Paul; Synthesis; vol. 49; 17; (2017); p. 3925 – 3930;,
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Synthetic Route of 455-68-5, The chemical industry reduces the impact on the environment during synthesis 455-68-5, name is Methyl 3-fluorobenzoate, I believe this compound will play a more active role in future production and life.

EXAMPLE 2 72.4 parts of methyl 3-fluorobenzoate are dissolved in 300 parts of 100percent strength sulfuric acid with stirring at not more than 30° C., the solution is cooled to 0°-10° C. and then, over the course of 2 hours, a mixture of 32.7 parts of 98percent strength nitric acid and 78.3 parts of 100percent strength sulfuric acid is added dropwise with continuous cooling at 0°-10° C., and the mixture is stirred without cooling for 3 hours, during which the temperature of the nitrating mixture rises to 20° C. Then 175 parts of water are added dropwise, again with continuous cooling. The methyl fluoronitrobenzoate separates out as an oil which is separated off, washed until neutral in portions with 350 parts of water, and dried in vacuo at 100° C. 92 parts of methyl fluoronitrobenzoate are obtained, comprising 98.1percent methyl 5-fluoro-2-nitrobenzoate and 1.9percent methyl 3-fluoro-2-nitrobenzoate, with an s.p. of 34.0° C. and a purity (GC) of >99percent based on isomer mixture.

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, Methyl 3-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoechst Aktiengesellschaft; US5543550; (1996); A;,
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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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H11NO2

General procedure: Water (4 mL) and HBF4 (~48-50% aq. sol., 4 mL) was added to the aniline (0.50 mmol, 1.0 equiv.) and stirred for a couple of minutes at room temperature in an open reaction flask. NaNO2 (0.038 g,1.1 equiv.) in water (2.8 mL) was added dropwise at 0C and stirred for 30 minutes. To the cold solution of the resulting diazonium salt was added sat. aq. copper(II)sulfate (50 mL), followed by copper(I)oxide (1.0 equiv., 0.072 g), and stirred at room temperature for 30 minutes. The reaction mixture was extracted with CH2Cl2, dried (MgSO4)and evaporated in vacuo. The crude products were purified by silica gel chromatography.Potential hazard note: Diazonium compounds can be explosive, however, the risk is greatly reduced by following several rules for precaution.[17]Additional points that render the experimental procedure reported herein safer is that the diazonium salt is prepared in situ under dilute conditions and is not isolated, the reaction is performed open to air, the reaction temperature is 0C to ambient, HBF4-is used as the counterion in this procedure, and arene diazonium tetra-fluoroborates, in contrast to the chloride salts, are renowned in general for their enhanced thermal stability and shockin sensitivity. Nevertheless, care should always be taken when handling diazonium compounds.

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; Kristianslund, Renate; Vik, Anders; Hansen, Trond V.; Synthetic Communications; vol. 48; 21; (2018); p. 2809 – 2814;,
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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. 4891-38-7, name is Methyl Phenylpropiolate, A new synthetic method of this compound is introduced below., COA of Formula: C10H8O2

General procedure: Steroidal/nonsteroidal bromo vinyl aldehyde (0.5 mmol), alkyne (0.5 mmol), benzyl amine (0.5 mmol), Pd(OAc)2 (5 mol%), PPh3 (10 mol%), Na2CO3 (1.5 mmol) and neutral alumina (200 mg) were mixed intimately and the mixture was irradiated in a closed vessel in a Synthos 3000 microwave reactor at 600 Watt (140 C and 12 bar) for 10 min. After 10 min ethylacetate (30 mL) was added to the reaction mixture and it was filtered through whatman filter paper. The residue obtained after removal of ethylacetate layer was purified by silica gel column chromatography using EtOAc/hexane as the eluent to afford the pyridine derivative. The alumina on the filter paper was then dried in vacuo and can be used again for another two times in place of Pd(OAc)2 without substantial loss of the yield of the product.

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; Shekarrao, Kommuri; Nath, Dipankar; Kaishap, Partha Pratim; Gogoi, Sanjib; Boruah, Romesh C.; Steroids; vol. 78; 11; (2013); p. 1126 – 1133;,
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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. 121-98-2, name is Methyl 4-methoxybenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H10O3

General procedure: A mixture of substrate (1 mmol), CuBr2 (22.4 mg, 10 mol%), LiBr (130.3 mg, 1.5 equiv.), and 0.05 mL of water was placed in a 50 mL stainless steel autoclave equipped with an inner glass tube in room temperature. CO2 (4 MPa) and O2 (1 MPa) were subsequently introduced into the autoclave and the system was heated under the predetermined reaction temperature for 15 min to reach the equilibration. Then the final pressure was adjusted to the desired pressure by introducing the appropriate amount of CO2. The mixture was stirred continuously for the desired reaction time. After cooling, products were diluted with acetone and analyzed by gas chromatograph (Shimadzu GC-2014) equipped with a capillary column (RTX-17 30 m × 25 mum and RTX-wax 30 m × 25 mum) using a flame ionization detector by comparing the retention times of authentic samples. The residue was purified by column chromatography on silica gel (200-300 mesh, eluting with petroleum ether/ethyl acetate from petroleum ether to 50:1) to afford the desired product. The isolated products were further identified with NMR spectra (Bruker 400 MHz) and GC-MS or GCD, which are consistent with those reported in the literature.

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:
Conference Paper; Liu, An-Hua; Ma, Ran; Zhang, Meng; He, Liang-Nian; Catalysis Today; vol. 194; 1; (2012); p. 38 – 43;,
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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 42726-73-8 as follows. Recommanded Product: tert-Butyl methyl malonate

Example 143B 1-tert-butyl 3-methyl 2-(6-ethoxy-5-nitropyridin-2-yl)malonate To a solution of Example 143A, 6-chloro-2-ethoxy-3-nitropyridine (3 g, 14.81 mmol), in N,N-dimethylformamide (30 mL) at 0° C. was added sodium hydride (1.185 g, 29.6 mmol), and the mixture was stirred for 20 minutes. Then, tert-butyl methyl malonate (3.16 mL, 17.77 mmol) was added dropwise, and the mixture was stirred at ambient temperature for 2 hours. The mixture was diluted with ether and quenched with H2O. The mixture was partitioned. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel eluting with 0-20percent ethyl acetate/heptanes to provide the titled compound.

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; AbbVie Inc.; Altenbach, Robert J.; Liu, Huaqing; Clapham, Bruce; Aguirre, Ana L.; Cowart, Marlon; Koenig, John R.; Sarris, Kathy; Scanio, Marc J.; Swinger, Kerren K.; Vasudevan, Anil; Villamil, Clara I.; Woller, Kevin R.; (95 pag.)US9777020; (2017); B2;,
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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. 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 3-ethoxy-3-iminopropionate hydrochloride

Step A:; The imidate salt 1g2(1.4 g, 7.2 mmol, 1 eq.) was combined with 2-(methylthio)aniline 111 (0.96 g, 7.50 mmol, 1 eq.) in ethanol (15 mL) under an N2atmosphere. The reaction mixture was stirred at RT (1 h) and monitored by HPLC.The reaction mixture was concentrated and then ether was added and the mixturefiltered. The solids were washed with ether and the combined ether washesconcentrated in vacua. The resulting adduct 112 was obtained as a yellow oil (1.66 g,82percent) and used as is in the next step. MS electrospray: (M + H)+; 282 and (M – H)”;280.

The synthetic route of 2318-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/7700; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, 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 4934-99-0, Recommanded Product: 4934-99-0

To a solution of methyl 3-hydroxycyclobutanecarboxylate AA28 (19.7 g, 152 mmol) in dichloromethane (200 mL) was added pyridine (90.0 g, 1.14 mol) , 4-dimethylaminopyridine (5.60 g, 45.6 mmol) and tosyl chloride (58.0 g, 303 mmol) at room temperature. After stirred at room temperature overnight, the mixture was poured water (200 mL) and extracted with ethyl ester (200 mL) twice. The combined organic layers were washed with 0.5 M hydrochloride aqueous solution (200 mL) , saturated sodium bicarbonate aqueous solution (200 mL) , water (200 mL) and brine (200 mL) , dried over Na2SO4 (s), filtered and the filtrate was concentrated under reduced pressure at room temperature to afford the title compound (42.7 g, 99 %yield) as yellow oil.1H NMR (300 MHz, CDCl3) delta 7.77 -7.73 (m, 2H) , 7.34 -7.26 (m, 2H) , 4.77 -4.64 (m, 1H) , 3.66 -3.59 (m, 3H) , 2.67 -2.54 (m, 1H) , 2.50 -2.37 (m, 7H) .

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, Methyl 3-hydroxycyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN SCIENCES IRELAND UNLIMITED COMPANY; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; JIANG, Yimin; WAN, Zhao-Kui; CHEUNG, Wing Shun; LIU, Qian; DENG, Gang; LIANG, Chao; (230 pag.)WO2019/214610; (2019); A1;,
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105-53-3, name is Diethyl malonate, 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. Recommanded Product: 105-53-3

The compound 1,1,1-triethoxyethane (62.6 mL, 341 mmol),Compound diethyl malonate (224.4 mL, 990.1 mmol),Acetic anhydride (1.4 mL, 10.1 mmol) and a catalytic amount of zinc chloride (0.1 g) were placed in a reaction flask and heated to 170 C for 5.0 h.Evaporating unreacted diethyl malonate under reduced pressure,The residue was purified by column (eluent: PE/EtOAc (v/v) = 20/1).40.0 g of yellow oil were obtained.The yield was 69.8%.

The synthetic route of 105-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ruyuan Yong Xing Technology Services Co., Ltd.; Liu Bing; Liu Jinlei; Zhang Yingjun; Zhang Jiancun; (158 pag.)CN104744446; (2019); B;,
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