Category: esters-buliding-blocks

Some common heterocyclic compound, 105-53-3, name is Diethyl malonate, molecular formula is C7H12O4, 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. category: esters-buliding-blocks

To a sodium ethoxide-ethanol solution, which was prepared by slowly addition sodium (8.625 g, 375 mmol) into ethanol (600 mL) in small pieces, was added diethyl malonate 283A (30 g, 187.5 mmol) at room temperature and stirred at room temperature for 20 minutes. To the solution was added 1,5-dibromopentane (45.29 g, 196.9 mmol) and stirred at reflux for 16 hours. The mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate (200 mL), washed with water (80 mL) and brine (50 mL x 2), dried over anhydrous sodium sulfate, filtered, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether from 0% to 10% v/v) to yield Compound 283B. LC-MS (ESI) m/z: 229 [M+H] ?H-NMR (CDC13, 400 IVII{z): (5(ppm) 1.25 (t, J 7.2 Hz, 6H), 1.40-1.46 (m, 2H), 1.50-1.55 (m, 4H), 1.96-1.99 (m, 4H), 4.18 (q, J= 7.2 Hz, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 105-53-3, its application will become more common.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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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 369-26-6 as follows. name: Methyl 3-amino-4-fluorobenzoate

Methyl 3-amino-4-fluorobenzoate (2 g, 13 mmol) and pyridine (2.1 g, 76.4 mmol) were suspended in DCM (25 mL), and to the stirring solution was slowly added 2-trifluoromethyl- benzenesulfonyl chloride (3.24 g, 13 mmol) at room temperature. After stirring for 2 h, the reaction mixture was washed with water and then extracted with DCM. The combined organic layers were dried over Na2SOzI, filtered, and concentrated in vacuo. The crude residue was suspended in water (30 mL) followed by slow addition of NaOH (1.1 g, 28 mmol), and the mixture heated at reflux overnight. After cooling to room temperature, the reaction mixture was extracted with DCM. The layers were separated. The aq. layer adjusted to pH 5 with aq. 5N HCl, and extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the final product as a solid (4.0 g, 83percent overall). LC-MS (ES) m/z = 364.1 (M+H)+ 1H NMR (400 MHz, DMSO-d6) delta ppm 10.61 (br, 1 H), 10.37 (br, 1 H), 8.78 (m, 1 H), 8.37 (m, 1 H), 8.01 (m, 2 H), 7.71 (m, 2 H), 7.31 (m, 2 H).

According to the analysis of related databases, 369-26-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; LAFRANCE, Louis, Vincent; LEBER, Jack, Dale; LI, Mei; VERMA, Sharad, Kumar; WO2010/126922; (2010); A1;,
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Electric Literature of 29263-94-3, 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. 29263-94-3 name is Diethyl 2-bromo-2-methylmalonate, 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: To a 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 2-bromo-2-methylmalonate, and friends who are interested can also refer to it.

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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Application of 17100-63-9,Some common heterocyclic compound, 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, molecular formula is C9H9BrO3, 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: A mixture of phenol (0.05 mol) (compounds 3, 8, 67, and 97-98), bromo-benzaldehyde (1.05 equiv.) (compounds 1-2, 9-12,48, 56, and 66), potassium carbonate (2 equiv.) and cupric oxide(0.3 equiv.) in pyridine (50 mL) was stirred under reflux for 12 h.The pyridine was distilled off in vacuo and the residue wasextracted with EtOAc (200 mL). The solution was concentrated andthe residue was purified by flash column chromatography (SiO2 orAl2O3), eluting with a hexane-DCM mixture, to yield the pureproduct as a solid in moderate yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-bromo-3-methoxybenzoate, its application will become more common.

Reference:
Article; Sun, Bin; Li, Lin; Hu, Qing-wen; Zheng, Hong-bo; Tang, Hui; Niu, Huan-min; Yuan, Hui-qing; Lou, Hong-xiang; European Journal of Medicinal Chemistry; vol. 129; (2017); p. 186 – 208;,
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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. 52787-14-1, name is Methyl 4-(2-methoxy-2-oxoethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C11H12O4

] the 23.0 NaH(1.2eq) and 600ml of anhydrous THF added into a 4L of reactor, cool down temperature to 0C, control the Temperature between 0 ~ 15 C then slowly dropping 100. 0 g of intermediate B of 300 mL THF solution and after the completion of addition the reaction was continued to stir for 0.5h ~ 1h.when the reaction was slowly cooled to -20 C ~ -15 C then slowly drop wise added 150mL THF solution of 62. 8 g (1. 1 eq.) 3-Bromo-1-propyne,agter the completion of addition slowly raise the temperature, at -20 C ~ -10 C the reaction was stirred for 1h, then at -10 C ~ 0 C the reaction was stirred for 2h and at 0 C ~ 10 C the reaction was stirred for 3h. The reaction was quenched with 400 mL of water and the intermediate C was extracted with ethyl acetate (400 mL X 2). The organic phase was washed with 200 mL of saturated sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated to dryness, stir beating with n-hexane, The filter cake was washed with a small amount of n-hexane to give a white solid C, Weight: 76. 4 g, yield: 64.5%, HPLC content: 95.3%

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 52787-14-1.

Reference:
Patent; SINOPHARM A THINK PHARMACEUTICAL CO LTD; (19 pag.)CN103739604; (2016); B;,
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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. 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, A new synthetic method of this compound is introduced below., Product Details of 23426-63-3

3 g of 5-tert-butyl-2-nitrophenol (15.37 mmol; 1.0 eq) were dissolved in 42 mL of DMF. 15 g of cesium carbonate (46.10 mmol; 3.0 eq) and 5.97 mL of methyl-2-bromo-2-methylpropanoate (46.10 mmol; 3.0 eq) were added and the session medium was stirred at 110 C. for 1 h. After cooling, the medium was diluted in water and the aqueous phase was extracted three times with EtOAc. The organic phases were washed with brine, dried over MgSO4, filtered and concentrated under vacuum, to give 5.11 g of the title compound in the form of a yellow oil. Yld: 100%. 1H NMR (300 MHz, DMSO-d6) deltappm 1.26 (s, 9H) 1.57 (s, 6H) 3.73 (s, 3 H) 6.87 (d, J=1.8 Hz, 1H) 7.23 (dd, J=8.5, 1.8 Hz, 1H) (d, J=8.5 Hz, 1H). LC-MS: m/z (M+H)+: 296.

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; INVENTIVA; BOUBIA, Benaissa; MASSARDIER, Christine; GUILLIER, Fabrice; POUPARDIN, Olivia; TALLANDIER, Mireille; AMAUDRUT, Jerome; BONDOUX, Michel; FEENSTRA, Roelof Williem; VAN DONGEN, Maria Johana Petronella; (207 pag.)US2017/66717; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10601-80-6, name is Ethyl 3,3-diethoxypropionate, 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 10601-80-6, Application In Synthesis of Ethyl 3,3-diethoxypropionate

To a 500 ml reaction flask was added 100 g of tetrahydrofuran, 10.0 g (0. 1 mol) of 3-acetoxypropylene,41. 8 g (0.22 mol) of ethyl 3, 3-diethoxypropionate, 5.2 g (30 mmol) of 47% boron trifluoride acetamidine solution,Nitrogen was replaced three times, and the temperature was raised to 60 C for 4 hours (recovery of diethyl ether). After completion of the reaction, the solvent was recovered, cooled to 20 C, and added20 g of water and 60 g of ethyl acetate were added and the layers were extracted with ethyl acetate and extracted three times (20 g each of ethyl acetate)The combined organic phase was dried over 20 g of anhydrous sodium sulfate for 4 hours, filtered and the ethyl acetate was recovered to give 2- ((4R, 6S) -6-acetoxyMethyl-2-ethoxycarbonylmethyl-1,3-dioxan-4-yl) acetate 27. 5 g, 98.9% purity (GC)82. 7%

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; XINFA PHARMACEUTICAL CO LTD; QI, YUXIN; LI, XINFA; LU, QIANGSAN; JU, LIZHU; (15 pag.)CN104163808; (2016); B;,
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Related Products of 383-62-0, These common heterocyclic compound, 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, 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.

Into a 250 ml 3-necked round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed NMP (80 ml). To the above was added KF (6.8 g, 0.12 mol) and CuI (15 g, 0.08 mol). After stirring 5-10 min, XIV-A-95 (11 g, 0.04 mol) and ClF2CCO2Et (18 g, 0.12 mol) were added. The resulting solution was stirred for 6 h while the temperature was maintained at 115-125 C. After cooling, 300 ml CH2Cl2 was added to the reaction system. The organic layer was washed with saturated NaCl solution (80 ml×5) and dried with Na2SO4. After evaporating the solvent, the residue was purified by column chromatography (eluant: PE_EtOAc=10:1) and compound XIV-B-95 was collected (4.65 g, 53.1%) as a yellow solid (m.p.: 38-40 C.)

The synthetic route of 383-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kalypsys, Inc.; US2005/234046; (2005); A1;,
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Application of 33491-30-4, 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. 33491-30-4 name is 8-Bromo-2H-chromen-2-one, 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.

(3) Weigh 1.8g of Br-C8 (8.89mmol),0.28 g of Pd(PPh3)4 (0.24 mmol) in a SCHLENK reaction tube under N2 atmosphere,35 mL of toluene was added, and 3.53 g of tri-n-butyl 2-pyridinium (9.60 mmol) was added dropwise.The reaction was stirred at 110 C for 16 h. After completion of the reaction, the mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure.It was separated and purified by silica gel column chromatography, and the mobile phase was dichloromethane.Finally, L-C8 was obtained as a white solid 1.49 g, and the yield was 83.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-2H-chromen-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Xi’an Jiaotong University; Zhou Guijiang; Feng Zhao; Yang Xiaolong; (40 pag.)CN109608502; (2019); A;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate, 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 145576-28-9, COA of Formula: C10H16O2

General procedure: The alkene (1.16 mmol, 1 equivalent) was dissolved in a vigorously stirred mixture of DCM (7 mL) and acetonitrile (7 mL) under nitrogen. 2,6-Lutidine (0.27 mL, 2.32 mmol, 2 equivalents), water (10.5 mL) and sodium periodate (993 mg, 4.64 mmol, 4 equivalents) were then added sequentially. The reaction concentration with respect to the alkene was 0.047 M in a mixture of 1: 1: 1.5 – DCM: acetonitrile: water. To the resulting mixture a stock solution of ruthenium(III) chloride trihydrate (0.035 M in water) (1.16 mL, 0.04 mmol, 3.5 mol %) was added dropwise via a syringe forming a brown suspension. The reaction was stirred vigorously at 20 C for 1 h (or for the time indicated in the Tables 2 and 3). The reaction was diluted with water (20 mL) then extracted with DCM (3 x 20 mL). The organic extracts were combined then washed with brine (20 mL), passed through a phase separating cartridge and the volatiles were removed under reduced pressure. The resulting residue was purified by flash silica chromatography (EtOAc / heptane) to afford the ketone.

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:
Article; Watson, David W.; Gill, Matthew; Kemmitt, Paul; Lamont, Scott G.; Popescu, Mihai V.; Simpson, Iain; Tetrahedron Letters; vol. 59; 51; (2018); p. 4479 – 4482;,
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