Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 17205-02-6, name is Ethyl 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 17205-02-6, Quality Control of Ethyl 3-hydroxycyclobutanecarboxylate

To a diethyl ether solution (30 mL) containing methyl magnesium bromide (7.63 mL of a 3.0 M diethyl ether solution) was added a diethyl ether solution (5 mL) containing ethyl 3- hydroxycyclobutane carboxylate (2.05 g, 6.94 mmol), dropwise. After two hours, the reaction was carefully quenched with 3 M aqueous hydrochloric acid. Magnesium sulfate was added until the evolution of gas stopped. The solution was filtered, and the solvent removed in vacuo yielding a viscous oil which was purified by silica gel chromatography, eluting with ethyl acetate:hexanes (1 :1 to 1 :0) to give 3-(2-hydroxypropan-2-yl)cyclobutanol (419 mg, 3.22 mmol, 46%). 1H NMR (CDCI3) delta 1 .13 (s, 6 H), 1 .74-1 .86 (m, 4 H), 2.23-2.39 (m, 2 H), 2.66 (br s, 1 H), 4.03-4.09 (m, 1 H).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, Dave Norman; SHEARER, Barry George; YOUNGMAN, Mark Andrew; (214 pag.)WO2018/229629; (2018); A1;,
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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. 14064-10-9, name is Diethyl 2-chloromalonate, A new synthetic method of this compound is introduced below., Computed Properties of C7H11ClO4

Example 15 Synthesis of ethyl 4-hydroxy-2-[2′-(trifluoromethyl)biphenyl-3-yl]-1,3-thiazole-5-carboxylate (15) 3-Bromobenzenecarbothioamide (1.00 g, 4.62 mmol) and diethyl chloropropanedioate (1.0 mL, 6.0 mmol) were dissolved in dioxane (35 mL). The mixture was heated at 80°C and stirred overnight, whereupon the solvent was removed under vacuum. Ethyl 2-(3-bromophenyl)-4-hydroxy-1,3-thiazole-5-carboxylate was obtained as a yellow solid (1.09 g, 72percent) by trituration in acetonitrile.

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; Dompe’ S.P.A.; Moriconi, Alessio; Bianchini, Gianluca; Colagioia, Sandro; Brandolini, Laura; Aramini, Andrea; Liberati, Chiara; Bovolenta, Silvia; EP2606888; (2013); A1;,
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Reference of 63485-50-7, 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. 63485-50-7, name is cis-Methyl 3-hydroxycyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Triphenylphosphine (830 mg, 3.16 mmol) was added to a solution of 4-fluoro-2- methoxyphenol (0.300 mL, 2.63 mmol) in tetrahydrofuran (2 mL). The reaction mixture was cooled to 0 C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (0.34 mL, 3.2 mmol) was added, followed by DIAD (0.61 mL, 3.2 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 12 h and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc (2X). The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 0%-50% EtOAc-hexanes gradient to give the title compound (666 mg, 100%). 1H NMR (400 MHz, CD3SOCD3) delta 2.24-2.40 (m, 2 H), 2.58 (ddd, J = 13, 7, 4 Hz, 2 H), 3.09-3.18 (m, 1 H), 3.62 (s, 3 H), 3.72 (s, 3 H), 4.71 (t, J = 7 Hz, 1 H), 6.56-6.66 (m, 1 H), 6.67-6.77 (m, 1 H), 6.88 (d, J = 3 Hz, 1 H); LC-MS (LC-ES) M+H = 255.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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Application of 927-68-4, 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 927-68-4 as follows.

EXAMPLE 128a Preparation of intermediate Acetic acid 2-(2-formyl-4-methyl-phenoxy)-ethyl ester To a solution of 2-hydroxy-5-methyl-benzaldehyde (2.4 g, 18 mmol) (Aldrich) in N,N-dimethylformamide (30 mL) was added cesium carbonate (6 g, 18 mmo), potassium iodide (3 g, 18 mmol) and 2-bromoethyl acetate (7 g, 42 mmol), Aldrich). The reaction mixture was heated at 100 C. for 3 h. The mixture was cooled to room temperature and diluted with ethyl ether, washed with water, brine, separated, and concentrated. The residue was purified by chromatography (EtOAc:Hexanes=1:6) to give acetic acid 2-(2-formyl-4-methyl-phenoxy)-ethyl ester as a yellow oil (Yield 4 g, 100%).

According to the analysis of related databases, 927-68-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chen, Li; Ding, Qingjie; Liu, Jin-Jun; Yang, Song; Zhang, Zhuming; US2007/213341; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4630-80-2, name is Methyl cyclopentanecarboxylate, 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 4630-80-2, category: esters-buliding-blocks

General procedure: Into an oven-dried reaction vial flushed with N2 were taken esters 8 (0.60 mmol) and anhydrous toluene (3.0 mL). The reaction vial was cooled to -78C and LDA (2M in THF, 0.36 mL) was added dropwise with stirring. After 1h at -78C, sulfinylimine 7 (0.5 mmol) dissolved in anhydrous toluene (2.0 mL) was added dropwise. Stirring was continued for 2 h with the temperature gradual rising to room temperature, then the reaction was quenched with saturated H2O (3.0 mL). The organic layer was taken and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered and the solvent was removed to give the crude product 9, which was purified by column chromatography (hexane/EtOAc, 4:1).

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, Methyl cyclopentanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dai, Yanling; Xie, Chen; Mei, Haibo; Han, Jianlin; Soloshonok, Vadim A.; Pan, Yi; Tetrahedron; vol. 71; 51; (2015); p. 9550 – 9556;,
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Adding a certain compound to certain chemical reactions, such as: 34846-90-7, name is Methyl 3-methoxyacrylate, 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 34846-90-7, HPLC of Formula: C5H8O3

A mixture of Intermediate-8C (1 equiv) and methyl 3-methoxyacrylate (3 equiv) was stirred at 90 °C for 6 h. The solvent was removed in vacuo and purification by silica gel chromatography (0-7percent methanol/dicloromethane) delivered the desired compound as a colorless solid (41percent). Intermediate-11: 1H NMR (400 MHz, CDC13) delta 10.46 (br s, 1H), 8.51 (d, 1H), 7.96 (d, 1H), 7.31 (s, 1H), 7.31-7.24 (m, 1H), 7.07-7.02 (m, 3H), 6.60 (d, 1H), 6.38 (d, 1H), 5.89 (s, 2H).

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; IRONWOOD PHARMACEUTICALS, INC.; KIM, Charles; NAKAI, Takashi; MOORE, Joel; PERL, Nicholas, Robert; IM, G-yoon, Jamie; BARDEN, Timothy, Claude; IYENGAR, Rajesh, R.; ZIMMER, Daniel, P.; FRETZEN, Angelika; RENHOWE, Paul, Allan; WO2013/101830; (2013); A1;,
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Some common heterocyclic compound, 5445-17-0, name is Methyl 2-bromopropanoate, molecular formula is C4H7BrO2, 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. Safety of Methyl 2-bromopropanoate

General procedure: To a solution of appropriate amount of 3-(arylimino)-2,3-dihydro-1H-isoindol-1-one 15 (0.75 mmol) in 10 cm3 dryacetone methyl 2-bromoalkanoate (1.12 mmol), 0.186 gpotassium iodide (1.12 mmol), and 0.207 g anhydrouspotassium carbonate (1.5 mmol) were added. The obtainedmixture was stirred at room temperature until the TLCshowed the absence of starting isoindolone 15(* 2-3 days). After that inorganic salts were filtered offand washed with 5 cm3 acetone. The filtrate was concentratedunder reduced pressure and the crude product waspurified by column chromatography (EtOAc/petroleumether 1:1) to afford the desired compound 16.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5445-17-0, its application will become more common.

Reference:
Article; Tkachuk, Volodymyr A.; Hordiyenko, Olga V.; Omelchenko, Irina V.; Medviediev, Volodomir V.; Arrault, Axelle; Monatshefte fur Chemie; vol. 149; 12; (2018); p. 2293 – 2309;,
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Related Products of 52273-79-7, 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. 52273-79-7, name is Ethyl 2-(3-aminophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6 N-(3-Ethoxycarbonylmethylphenyl)-L-glutamine: Compound (6) Following the procedure described in (a) of Example 1, 11.14 g (0.03 mole) of N-carbobenzoxy-L-glutamic acid alpha-benzyl ester was reacted with 4.96 g (0.03 mole) of ethyl m-aminophenylacetate to give 12.95 g (81% yield) of an intermediate. The intermediate was dissolved in 500 ml of tetrahydrofuran, 200 ml of ethanol and 100 ml of water. To the solution was added 0.3 g of palladium black and the mixture was subjected to hydrogenation at atmospheric pressure to give 6.58 g (89% yield) of N-(3-ethoxycarbonylmethylphenyl)-L-glutamine, m.p. 175.5-176.2 C. [alpha]D25 =+26.4 (c=1 2 N HCl)

The synthetic route of Ethyl 2-(3-aminophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Chemical Industries Ltd.; Nippon Shinyaku Co., Ltd.; US4439448; (1984); A;,
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Electric Literature of 25597-16-4, 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 25597-16-4 as follows.

Step 5: ethyl 6,8-(dimethyl-D6)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (2.02 g, 0.013 mol) from step 4, ethyl 4,4,4-trifluorocrotonate (4.30 g, 0.026 mol) and anhydrous potassium carbonate (1.76 g, 0.013 mol) were dissolved in DMF (70 mL), and then the system was stirred for 6 hrs at 80 C. At the end of reaction, the reaction system was cooled to room temperature, added with water and then extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 2.35 g of the product (60.1%) by column chromatography. 1HNMR (400 MHz, d6-DMSO), delta ppm 7.84 (s, 1H), 7.13 (s, 1H), 7.09 (s, 1H), 5.94 (m, 1H), 4.25 (dd, 1H), 1.27 (t, 3H)

According to the analysis of related databases, 25597-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences; Zhang, Yanmei; Talley, John Jeffrey; Obukowicz, Mark G.; Tu, Zhengchao; Tortorella, Micky; Wang, Yican; Liu, Jianqi; Chen, Yan; Liu, Xiaorong; Lu, Xin; US2015/133538; (2015); A1;,
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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 7778-83-8 as follows. Application In Synthesis of Propyl 3-Phenylacrylate

The substrate is used cinnamic acidPropyl ester (47.6mg, 0.2mmol) and (S) -1,1′- binaphthyl-2,2′-diyl hydrogen phosphate (73.1mg, 0.21mmol, 1.01Equiv.), Was addedAfter N- bromosuccinimide, 30h is reacted, and other experimental conditions were the same method as in Example 1, to obtain a colorless oily liquid 97.2mg, yield 70.7%.Two non enantiomers by high performance liquid chromatography )The chalcone (41.6mg, 0.2mmol) and (R / S) -1,1′- binaphthyl-2,2′-diyl hydrogen phosphate (73.1mg, 0.21mmol, 1.01Equiv.) Was dissolved in 2mLTHF ; and at room temperature, under argon atmosphere, was slowly every 2hWas added N- bromosuccinimide (0.1mmol, 0.5Equiv.) For a total of 4 times was added, N- bromosuccinimide was added, reaction was continued for 24h, the solvent was removed under reduced pressure, the residue by column chromatography gel (ethyl acetate: n-hexane; (1: 10, V / V, 100mL), (1: 5, V / V100mL), (1: 3, V / V, 200mL)), to give a colorless oily liquid121.7mg, yield 86%.The product form two diastereomers by high performance liquid.

According to the analysis of related databases, 7778-83-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dalian Institute of Chemical Physics; Zhao, Zongbao; Suo, Heier; Liu, Wujun; (44 pag.)CN105524110; (2016); A;,
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