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. 5326-50-1, name is Ethyl 2-(1-hydroxycyclohexyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H18O3

Reference Example 62; [1-(Benzoylamino)cyclohexyl]acetic acid; To a mixture of ethyl (1-hydroxycyclohexyl)acetate (17.1 g, 92.1 mmol) and benzonitrile (9.5 ml, 92.1 mmol) was added conc. sulfuric acid (50 ml) at 0C, and the mixture was stirred at room temperature for 12 hrs. Water (200 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, and then with saturated brine and dried over anhydrous MgS04. After concentration under reduced pressure, ethanol (50 ml) and 50% aqueous potassium hydroxide solution (10 ml) were added to the residue, and the mixture was heated under reflux for 6 hrs. Water (400 ml) was added to the reaction mixture, and the mixture was washed with diethyl ether. The aqueous layer was acidified (pH 2) with 5N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The obtained solid was recrystallized from ethanol-toluene to give the title compound (18.1 g, 75%) as colorless crystals. ?H-NMR (CDCl3) No.:1.14-1.62 (8H, m) , 2.25-2.43 (2H, m) , 2.74 (2H, s), 3.32 (lH, s), 7.36-7.57 (3H, m), 7.73-7.80 (2H, m), 11.93 (lH, s). LC/MS (ESI) m/z: 262 (MH(at)).

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 5326-50-1.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2005/105802; (2005); 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 22223-49-0 as follows. HPLC of Formula: C9H11NO2

The mixture of pyridine-4-carboxylic acid (1.1199g; 9.0967mmol) dissolved in thionyl chloride (15mL; 206.7748mmol) were mixed and refluxed for 1-3h. Then the excess of thionyl chloride was distilled under vacuum and the aromatic amine methyl ester Ea (1.500g; 9.0816mmol) dissolved in CHCl3 (20mL; 249.6231mmol) was added. The mixture was heated and stirred under reflux for 3-6h. The amide (L2: yield ca. 50%; 1.2212g; 3.5627mmol) was precipitated as yellow crystals after washing the dark yellow oil with diethyl ether and recrystallization with the mixture of acetone and methanol (m.p. 180C). Anal. Calc. for (C15H15N2O3)Cl(H2O)2: C, 52.56; H, 5.59; N, 8.17. Found: C, 52.39; H, 6.30; N, 8.16. FT-IR (KBr): 3435cm-1 nu(O-H), 3218cm-1 nu(N-H), 3056, 2924, 2852cm-1 nu(C-H), 1730 and 1640cm-1 nu(C=O), 1603-1441cm-1 nu(ringC=C), 1317-1088cm-1 nu(C-O) and nu(C-N) overlapped, 803/750cm-1 delta(ringC=C)oop. 1H NMR (403MHz, d-DMSO, ppm) delta: 10.71 (s, 1H) – 9, 9.04 (dd, J=4.98, 1.52Hz, 2H) – 2/4, 8.28 (dd, J=4.96, 1.54Hz, 2H) -1/5, 7.71 (m, 1H) – 14, 7.57 (ddd, J=7.64, 1.53, 0.72Hz, 1H) – 12, 7.38 (t, 1H) – 13, 4.41 (s, 12H N+-H protone – fast chemical exchange with water molecules) – 3, 3.72 (s, 3H) – 20, 2.30 (s, 3H) -16. 13C NMR (151MHz, d-DMSO, ppm) delta: 166.32-17, 162.88-7, 146.52-2/4, 145.42-6, 136.54-11, 134.61-10, 134.33-12, 128.25-15, 127.95-14, 126.95-13, 123.44-1/5, 52.10-20, 17.86-16.

According to the analysis of related databases, 22223-49-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kwiatek, Dorota; Kubicki, Maciej; Barczy?ski, Piotr; Lis, Stefan; Hnatejko, Zbigniew; Journal of Molecular Structure; vol. 1145; (2017); p. 86 – 93;,
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Reference of 454-31-9, 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. 454-31-9, name is Ethyl 2,2-difluoroacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 16 (3.2 g, 0.0123 mol) was stirred in toluene (150 mL) at 0C under N2. Potassium tert-butoxide (1.94 g, 17.3 mmol) was added at 0-5C, ethyldifluoroacetate (1.84 g, 0.0149 mol) was added dropwise at 0-5C. RM was stirred at RT for 2 hr. The RM was washed with 10% H2S04 in water and the OL was dried on MgS04, filtered and evaporated to yield intermediate 17 (4.16 g, 99%).

The synthetic route of Ethyl 2,2-difluoroacetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN ROOSBROECK, Yves, Emiel, Maria; VAN DEN KEYBUS, Frans, Alfons, Maria; TRESADERN, Gary, John; BUIJNSTERS, Peter, Jacobus, Johannes, Antonius; VELTER, Adriana, Ingrid; JACOBY, Edgar; MACDONALD, Gregor, James; GIJSEN, Henricus, Jacobus, Maria; AHNAOU, Abdellah; DRINKENBURG, Wilhelmus, Helena, Ignatius, Maria; (216 pag.)WO2018/83098; (2018); A1;,
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These common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, 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. Recommanded Product: Methyl 3-bromopropiolate

Into a 50-mL round-bottom flask, was placed tert-butyl 1H-pyrrole-1-carboxylate (3) (14.4 g, 86.12 mmol, 3.00 equiv), methyl 3-bromoprop-2-ynoate (2) (4.7 g, 28.84 mmol, 1.00 equiv). The resulting solution was stirred for 20 h at 90 C. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:30?1:15) as eluent to furnish 2.89 g (30%) of 7-tert-butyl 2-methyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate (4) as a yellow oil.

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

Reference:
Patent; YEE, Calvin W.; Li, Zhe; US2015/141465; (2015); 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. 369-25-5, name is Methyl 3,4-difluorobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6F2O2

[0620] tert-Butyl 4-(2-fluoro-4-(methoxycarbonyl)phenyl)piperazine-l-carboxylate (301): Potassium carbonate (5.56 g, 40.3 mmol) and tert-bvXy piperazine-1-carboxylate (6.92 g, 37.2 mmol) were combined; methyl 3,4-difluorobenzoate (5.33 g, 31.0 mmol) was added, and the reaction mixture was stirred at 900C for 1 d. The mixture was triturated with ethyl acetate (3 x 5 mL) and the combined organic extracts were filtered, concentrated down to about 5-10 mL, and subjected to flash column chromatography on silica gel (120 g SiO2, hexanes:ethyl acetate 1 :0 to 4:1) to afford the title compound as a white solid (4.702 g, 13.90 mmol, 44.9 % yield). ESI-MS: m/z 339 (M+H)+.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; GANGLOFF, Anthony, R.; JENNINGS, Andrew, John; VU, Phong, H.; WO2010/111626; (2010); A2;,
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Reference of 5335-05-7, 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. 5335-05-7 name is Chloromethyl benzoate, 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.

Into 2 ml of N,N-dimethylformamide was suspended 0.05 g of sodium hydride (60% oily), and 0.2 g of 3-(4-trifluoromethylpyridin-2-yl)-l,2,4-oxadiazol-5-one was added at room temperature. After stirring for 10 minutes, 0.18 g of chloromethylbenzoate, and the mixture was stirred at 70C for 3 hours. The reaction solution was allowed to cool to room temperature, and poured into an aqueous saturated ammonium chloride solution, followed by extraction with ethyl acetate three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.12 g of [3-(4- trifluoromethylpyridin-2-yl)- 1 ,2,4-oxadiazol-5-on-4-yl]methyl=benzoate (present compound (27)).Present Compound (27)1H-NMR: 6.44 (s, 2H), 7.38-7.42 (m, 2H), 7.53-7.59 (m, IH), 7.71 (d, IH), 7.79-7.92 (m, 2H), 8.30 (s, IH), 8.87 (d, IH)

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

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/66786; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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

General procedure: A mixture of Yb(OTf)3 (2.5 mol%), amine (1.0 eq.), ethyl 3,3-diethoxypropionate (2.5 eq.) and aldehyde (1.1 eq.) in 1,4-dioxane (1.5 mL / 1 eq.) was stirred at 90 C for 6-17 h. After the reaction, the resulting mixture was washed with PBS buffer solution (25 mL) and extracted with CH2Cl2 (15 mL¡Á3). The organic layer was dried over MgSO4. Removal of the solvent in vacuo, followed by chromatography on silica gel column (AcOEt/Hexane or CHCl3/MeOH), afforded dihydropyridine 4.

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

Reference:
Article; Sueki, Shunsuke; Takei, Ryo; Abe, Junya; Shimizu, Isao; Tetrahedron Letters; vol. 52; 34; (2011); p. 4473 – 4477;,
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Reference of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 1Mixture of dimethyl fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl]propanedioate (8a) and dimethyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]propanedioate (8b) 23.81 g (110.2 mmol) of a 25 w/w % methanol solution of sodium methoxide (NaOMe) was added to a methanol (90.4 mL) solution of 18.19 g (121.2 mmol) of dimethyl fluoropropanedioate (7) over 3 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring the solution thus obtained for 15 minutes, 4.52 g (55.1 mmol) of 6-oxabicyclo [3.1.0] hex-2-ene (6) was added thereto over 2 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring at room temperature for 1 hour, 45 mL of a saturated ammonium chloride aqueous solution was added over 10 minutes while keeping the internal temperature between 26 C. and 35 C. The reaction mixture was concentrated under reduced pressure, most of the methanol was removed by evaporation, and 108 g of a brown solution containing solids was obtained. After extraction with 136 mL of ethyl acetate was carried out twice, washing with 45 mL of water was carried out. After the organic layer was concentrated under reduced pressure, 100 mL of toluene was added, and concentration under reduced pressure was carried out again. The concentrated residue was purified by flash silica gel column chromatography (eluent:toluene/ethyl acetate), thus giving 7.21 g of a mixture of the compound of the formula 8a and the compound of the formula 8b as a yellow oily substance.1H NMR (500 MHz, DMSO-d6): delta (ppm) 2.13-2.17 (m, 1H), 2.56 (dddd, J=2.2, 4.3, 7.1, 17.2 Hz, 1H), 3.32-3.40 (m, 1H), 3.77 (s, 3H), 3.79 (s, 3H), 4.20 (m, 1H), 5.04 (d, J=6.1 Hz, 1H), 5.47 (ddd, J=2.1, 4.3, 6.1 Hz, 1H), 5.85 (ddd, J=2.2, 4.4, 6.1 Hz, 1H). 13C NMR (125 MHz, DMSO-d6): delta (ppm) 41.93, 53.39 (d, J=19.5 Hz), 58.70 (d, J=20.8 Hz), 70.43 (d, J=2.6 Hz), 93.55, 95.14, 125.59, 133.32, 165.42 (d, J=15.6 Hz), 165.62 (d, J=14.3 Hz). 19F NMR (470 MHz, DMSO-d6): delta (ppm) -172.43, -172.36. HRMS(ES)m/z: [M+Na]+ calcd for CHH13O5FNa; 255.0645, found 255.0635. IR (neat) 3528, 3408, 2960, 1755, 1438, 1284, 1253, 1173, 1111, 1068, 1031, 936, 838, 787, 722, 668, 415 cm-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, Dimethyl 2-fluoromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; US2012/232304; (2012); A1;,
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Related Products of 25662-28-6, 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. 25662-28-6, name is Methyl 1-cyclopentene-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under nitrogen atmosphere, a mixture of in H2O (0.90muL, 0.050mmol) in THF (1mL) was added to an oven-dried reaction tube charged with (R)-H8-BINOL (22.1mg, 0.075mmol). After stirred at RT for 5min, Bu2Mg (1.0M in heptane, 50.0muL, 0.050mmol) and diarylphosphine oxide (3, 0.50mmol, 0.5M in anhydrous THF) were sequentially added and stirred for another 5min before being cooled to-20C. alpha,beta-Unsaturated ester (2, 0.50mmol) was then added, and the reaction was stirred at-20C for 2-3 days. The reaction mixture was quenched with sat. NH4Cl (2mL), diluted with H2O (5mL) and extracted with CH2Cl2 (10mL¡Á2). The combined organic phase was dried over anhydrous Na2SO4. After filtration and concentration, and the residue was purified by silica gel column chromatography (hexane: THF=5:1 to 1:1) to give the corresponding product. The enantiomeric excess was determined by the chiral HPLC analysis.

The synthetic route of Methyl 1-cyclopentene-1-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cao, Meng-Yue; Xu, Zhi-Min; Gao, Wei; Liu, Juan; Tan, Fen; Lu, Hai-Hua; Tetrahedron; vol. 75; 24; (2019); p. 3282 – 3291;,
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Adding a certain compound to certain chemical reactions, such as: 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, 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 383-62-0, COA of Formula: C4H5ClF2O2

EXAMPLE 174(R)-5-(5-(Difluoromethoxy)pyrimidin-2-yloxy)-N-(4-(morpholin-2-yl)phenyl)pyrimidin-2-aminea) 2-Chloro-5-(5-(difluoromethoxy)pyrimidin-2-yloxy)pyrimidine2-Chloropyrimidin-5-ol (0.5 g) was combined with DMF (5 ml) to give a colourless solution. K2CO3 (582 mg) and ethyl 2-chloro-2,2-difluoroacetate (534 mul) were then added. The reaction mixture was stirred at 70 C. overnight to afford a brown suspension. The reaction mixture was then poured into EtOAc and washed sequentially with water and with saturated brine. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel; gradient: 0% to 60% EtOAc in hexanes) to afford 2-chloro-5-(5-(difluoromethoxy)pyrimidin-2-yloxy)pyrimidine (154 mg, 15%) as a yellow solid. MS (ISP): 277.0 ([{37Cl}M+H]+), 275.0 ([{35Cl}M+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; Galley, Guido; Norcross, Roger; Pflieger, Philippe; US2012/245172; (2012); A1;,
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