Tag: M.W=100-200

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. 454-31-9, name is Ethyl 2,2-difluoroacetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H6F2O2

Intermediate 15 (2.57 g, 0.0101 mol) was stirred in toluene (150 mL) at 0C under N2. Potasssium tert.-butoxide (1.59 g, 14.2 mmol) was added at 0-5C, ethyldifluoroacetate (1.52 g, 0.0122 mol) was added dropwise at 0-5C. RM was stirred at RT for 2 h. The RM was washed with 10%> H2SO4 in water and the OL was dried on MgS04, filtered and evaporated to yield intermediate 16 (3.34 g, 99%).

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; JANSSEN PHARMACEUTICA NV; VAN ROOSBROECK, Yves, Emiel, Maria; BUIJNSTERS, Peter, Jacobus, Johannes, Antonius; TRESADERN, Gary; JACOBY, Edgar; OEHLRICH, Daniel; GIJSEN, Henricus, Jacobus, Maria; (67 pag.)WO2018/83103; (2018); A1;,
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Related Products of 711-01-3, 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 711-01-3 as follows.

General procedure: 1 equiv. substrate, 2 equiv. TsCN, 1 equiv CAN, 1 equiv Li2CO3, 0.2 equiv. NHPI and 5 mL DCE were stirred for 16 h at 75 ¡ãC. After 6 h 0.2 equiv. NHPI were added. The reactions mixture was allowed to cool down to room temperature andfiltered over silica gel (50 mL EtOAc, 50 mL MeCN, 50 mL EtOAc).

According to the analysis of related databases, 711-01-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Berndt, Jan-Philipp; Erb, Frederik R.; Ochmann, Lukas; Beppler, Jaqueline; Schreiner, Peter R.; Synlett; vol. 30; 4; (2019); p. 493 – 498;,
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These common heterocyclic compound, 5445-17-0, name is Methyl 2-bromopropanoate, 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. Computed Properties of C4H7BrO2

Add p-chlorodiphenyl disulfide (0.5 mmol) to a 10 mL reaction tube.Methyl alpha-bromopropionate (1.0 mmol),Zinc powder (2.0 mmol) solvent toluene (2 mL) and dinuclear Schiff base titanium perfluorooctanesulfonic acid complex (X=OSO2C8F17)(0.04 mmol), stirred for 4 h at 25C. Spin dry after the reaction is over.The residue was extracted with ether three times and the filtrate was evaporatedThe crude product was separated by silica gel column chromatography.This gave methyl 2-p-chlorophenylthiopropionate as a colorless oily liquid in a yield of 86%.

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

Reference:
Patent; Shanxi Medical University; Li Ningbo; Wang Lingxiao; Wang Haojiang; Zhao Wenjie; (13 pag.)CN107722049; (2018); A;,
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Related Products of 41658-03-1, These common heterocyclic compound, 41658-03-1, name is Ethyl 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.

General procedure: A dry and argon flushed Schlenk-flask, equipped with a magnetic stirring bar and a rubber septumwas charged with 1,8-bis(butylthio)-3,6-dichloro-2,7-naphthyridine (1.0 equiv) in THF. After cooling to-40 C, a solution of TMPLi (1 M in THF, 1.2 equiv) was slowly added. The reaction mixture wasstirred for 30 min at the same temperature. Then, the corresponding electrophile (1.2 equiv) wasadded and the solution was stirred at -40 C until complete conversion of the starting material(detected by GC-analysis of reaction aliquots).

The synthetic route of 41658-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Greiner, Robert; Blanc, Romain; Petermayer, Christian; Karaghiosoff, Konstantin; Knochel, Paul; Synlett; vol. 27; 2; (2016); p. 231 – 236;,
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Adding a certain compound to certain chemical reactions, such as: 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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 816-27-3, name: Ethyl 2-ethoxy-2-iminoacetate

To a solution of cis-1-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (9.5 g, 31.0 mmol) in ethanol (250 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.7 g, 46.5 mmol). The reaction mixture was stirred at 60 C. for 6 h and subsequently concentrated under reduced pressure to afford crude ethyl 2-[[cis-3-[tert-butyl(dimethyl)silyl]oxy-2-oxo-5-phenyl-pyrrolidin-1-yl]amino]-2-imino-acetate as a yellow oil (10.6 g, 84%), used in the next step without further purification. LCMS RT=2.106 min, m/z=406.2 [M+H]-. LCMS (10 to 80% acetonitrile in water+0.1% ammonia water over 3.0 mins) retention time 2.106 mm, ESI+ found [M+H]=406.2.

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, Ethyl 2-ethoxy-2-iminoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (2018); A1;,
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Application of 89-71-4, 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 89-71-4 as follows.

A mixture of methyl o-toluate (13.5 g, 89.9 mmol), NBS (17.6 g, 98.9 mmol), and benzoyl peroxide (50 mg, 0.2 mmol) in carbon tetrachloride (250 mL) was heated at reflux over the weekend. The reaction mixture was allowed to cool, and it was then filtered. The solvents were evaporated under reduced pressure and the residue was purified by chromatography, eluting with 3% ethyl acetate/hexanes to give 2-bromomethyl-benzoic acid methyl ester (7.7 g, 37%) as a white solid. 1HNMR (CDCl3): delta 7.97 (dd, J=1.5 Hz, 8.0 Hz, 1H), 7.49 (m, 2H), 7.38 (dt, J=1.5 Hz, 8.0 Hz, 1H), 4.96 (s, 2H), 3.94 (s, 3H). MS (APCI+): 231 (100), 229 (93).

According to the analysis of related databases, 89-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chu, Chang An; Gillespie, Paul; Tilley, Jefferson Wright; US2004/266856; (2004); A1;,
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Application of 35179-98-7, These common heterocyclic compound, 35179-98-7, name is Chloromethyl ethyl carbonate, 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.

ELQ-300 (0.85 g, 1.8 mmol), tetrabutylammonium iodide (1.33 g, 3.6 mmol) and potassium carbonate (0.50 g, 3.6 mmol) were dissolved anhydrous dimethylformamide (8 ml) in a flame-dried round bottom flask at 60 C under inert atmosphere. Chloromethyl ethyl carbonate (0.5 g, 3.6 mmol) was added dropwise and the reaction stirred under inert atmosphere at 60 C for two hours, at which point reaction completion was confirmed by thin layer chromatography. After cooling to room temperature, the reaction solvent was removed under reduced pressure and the mixture taken up in water (10 ml) and extracted with dichloromethane (3 x 20 ml). Combined organic layers were washed with brine (10 ml), dried over MgS04, and the dichloromethane evaporated under reduced pressure. The resulting crude product was purified by flash chromatography (EtOAc/DCM) to yield the title compound, ELQ- 331, as a white crystalline solid (560 mg, 54%). 1H NMR (400 MHz, DMSO-d6): delta = 7.98 (s, 1H), 7.57 (s, 1H), 7.44 (m, 4H), 7.21 (m, 4H), 5.76 (s, 2H), 5.35 (s, 2H), 4.03 (s, 3H), 2.44 (s, 3H), 1.11 (t, 3H, J = 7.1 Hz); M.P. (C): 103.5-103.7.

Statistics shows that Chloromethyl ethyl carbonate is playing an increasingly important role. we look forward to future research findings about 35179-98-7.

Reference:
Patent; OREGON HEALTH & SCIENCE UNIVERSITY; THE UNITED STATES GOVERNMENT AS REPRESENTED BY THE DEPARTMENT OF VETERANS AFFAIRS; RISCOE, Michael; NILSEN, Aaron; STICKLES, Allison; MILEY, Galen; WINTER, Rolf; POU, Sovitj; LI, Yuexin; KELLY, Jane Xu; FORQUER, Isaac; DOGGETT, J. Stone; BRUZUAL, Igor; FRUEH, Lisa; DODEAN, Rozalia; SMILKSTEIN, Martin; ALDAY, Holland; KOOP, Dennis; BLEYLE, Lisa; (43 pag.)WO2017/15360; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6914-71-2, name is 1,1-Cyclopropanedicarboxylic acid dimethyl ester, 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 6914-71-2, Application In Synthesis of 1,1-Cyclopropanedicarboxylic acid dimethyl ester

Synthesis of Cyclopropane-1,1-dicarboxylic acid methyl ester KOH (42 mg, 0.75 mmol) was added to a solution cyclopropane-1,1-dicarboxylic acid dimethyl ester (100 mg, 0.63 mmol) in methanol. The resulting mixture was stirred for 4 hours at ambient temperature then concentrated. The residue was diluted with water, acidified with conc. HCl and the product was extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford 65 mg (71%) of cyclopropane-1,1-dicarboxylic acid methyl ester.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Cyclopropanedicarboxylic acid dimethyl ester, and friends who are interested can also refer to it.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; US2009/239848; (2009); A1;,
Ester – Wikipedia,
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Reference of 431-47-0, These common heterocyclic compound, 431-47-0, name is Methyl 2,2,2-trifluoroacetate, 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.

Phthalimide (100 mg, 0.68 mmol), DMSO (10 mL), CH3ONa (112 mg, 2 mmol, 3 eq.) was added to the reaction flask in turn, stirred at room temperature for 5 minutes, and then uniformly dispersed after NaH. Methyl trifluoroacetate (0.28 mL, 2.7 mmol, 4 eq.) was slowly injected into the reaction flask. After reacting for 10 hours, the TLC was plated, and the starting point disappeared, that is, the reaction was completed, and the stirring was stopped. Extract twice with ethyl acetate and distilled water, then wash with saturated NaCl solution. The organic phases were combined, and the organic phase was dried over anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration, and the solvent was evaporated. Purification by column chromatography gave white solid N-methylphthalimide (109 mg,Yield 100%).

The synthetic route of 431-47-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Petrochemical College; Xiao Duoduo; Zheng Xin; Zeng Jiechun; Huang Jiawei; Zhou Rujin; Guan Ying; Liang Jieling; (8 pag.)CN109369506; (2019); A;,
Ester – Wikipedia,
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Synthetic Route of 25597-16-4,Some common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, 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.

To a solution of LiAlH4 (1.35g, 35.5mmol, 1.5equiv.) in dry Et2O (13.0mL) under argon atmosphere was added dropwise a solution of AlCl3 (2.22g, 16.6mmol, 0.7equiv.) in dry Et2O (6.5mL). After 20min of stirring at 0C, a solution of ethyl (E)-4,4,4-trifluorocrotonate (4.00g, 23.8mmol, 1.0 equiv.) in dry Et2O was added dropwise. The resulting mixture was allowed to stir at 0C for 2 h. A saturated aqueous solution of Na2SO4 was then added (Caution: very exothermic reaction). The mixture was filtrated and the solid was washed several times with Et2O. The organic layers were combined and washed with brine and dried over MgSO4. Solvent was removed by thorough distillation at atmospheric pressure to afford (E)-4,4,4-trifluorobut-2-en-1-ol (7) as a colorless oil which was used without any further purification.

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

Reference:
Article; Forcellini, Elsa; Hemelaere, Remy; Desroches, Justine; Paquin, Jean-Francois; Journal of Fluorine Chemistry; vol. 180; (2015); p. 216 – 221;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics