Month: July 2021

Related Products of 10601-80-6, 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. 10601-80-6 name is Ethyl 3,3-diethoxypropionate, 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 mixture of montmorillonite K-10 (75 mg), an appropriate aniline 1 (150 mg, 1.2 mmol), ethyl-3,3-diethoxypropionate (3) (579 mg, 3 mmol) and an aldehyde (166 mg, 1.34 mmol) in pure water (7.5 mL) was stirred at 90 C for the time mentioned in Table 2. After completion of the reaction (indicated by TLC), the mixture was cooled to room temperature and filtered. The filtrate was extracted with EtOAc (3 × 5 mL). The organic layers were collected, combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-hexane to give the desired product.

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; Reddy, T. Ram; Reddy, G. Rajeshwar; Reddy, L. Srinivasula; Meda, Chandana Lakshmi T.; Parsa, Kishore V.L.; Kumar, K. Shiva; Lingappa; Pal, Manojit; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 395 – 404;,
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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. 15224-11-0, name is Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 15224-11-0

General Procedure 61 Ethyl 2-[(4-bromo-1H-pyrazol-1-yl)methyl]cyclopropanecarboxylate (4-3): To a reaction solution of ethyl 2-(hydroxymethyl)cyclopropanecarboxylate (4-1) (577 mg; 4.0 mmol) with Et3N (1.1 mL; 8.0 mmol) and DMAP (49 mg; 0.4 mmol) in 12 mL of CH2Cl2 at 0 C. was added methanesulfonyl chloride (0.4 mL; 4.8 mmol). The resulting mixture of brown color suspension was stirred at 0 C. to room temperature under N2 for overnight. The reaction mixture was quenched with NaHCO3, then partitioned between CH2Cl2 (200 mL) and saturated NaHCO3 solution (50 mL); brine (50 mL). The organic layer was dried (Na2SO4), then filtered through silica gel pad, eluted with hexane:EtOAc/1:1. The filtrate was concentrated by vacuum to give 880 mg of ethyl 2-{[(methylsulfonyl)oxy]methyl}cyclopropanecarboxylate as a yellow oil (99% yield). 1H NMR (400 MHz, chloroform-D) delta ppm 0.91-1.02 (m, 1H) 1.26 (q, J=6.99 Hz, 3H) 1.29-1.36 (m, 1H) 1.63-1.74 (m, 1H) 1.79-1.92 (m, 1H) 3.02 (s, 3H) 3.99-4.24 (m, 4H).

The synthetic route of 15224-11-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (2006); A1;,
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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. 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1000342-11-9

[01042] Step 5: methyl l-acetyl-6-bromo-lH-indazole-4-carboxylate[01043] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (15 g, 61.5 mmol) in chloroform (150 mL), was added potassium acetate (6.32 g, 64.4 mmol) and acetic anhydride (12.6 g, 122.9 mmol) and reaction mixture was stirred at room temperature for 12 h. After this time, tert-butyl nitrite (25.3g, 246.1 mmol) and 18-crown-6 (5.7 g, 21.5 mmol) were added and reaction stirred again at 65 C for 3 h. On completion, the reaction mass was cooled to room temperature, diluted with chloroform (500 mL) and washed with sat. sodium bicarbonate solution. The organic layer was dried over sodium sulfate and concentrated to afford the title compound (18 g, 98.3%).

According to the analysis of related databases, 1000342-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EPIZYME, INC.; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; CHESWORTH, Richard; DUNCAN, Kenneth, William; WO2012/118812; (2012); A2;,
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Synthetic Route of 14062-25-0, These common heterocyclic compound, 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, 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.

2.0 M LDA in heptane/THF/ethylbenzene (6.0 mL, 12 mmol) was slowly added to a solution of ethyl (4-bromophenyl)acetate (2.43 g, 10.0 mmol) in THF (20 mL) at -78 C. and then the mixture was stirred for 30 min. Methyl iodide (0.93 mL, 15 mmol) was added at -78 C. and then the reaction was stirred for an additional 30 min. Saturated NH4Cl aq. was added to quench the reaction. The mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-10%) to afford the desired product (2.0 g).

The synthetic route of 14062-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YAO, Wenqing; ZHANG, Colin; XU, Meizhong; ZHUO, Jincong; HE, Chunhong; US2012/165305; (2012); 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. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, A new synthetic method of this compound is introduced below., Computed Properties of C9H11NO2

A solution of 3 (244 mg, 1 mmol), methyl 4-(aminomethyl)benzoate 8 (198 mg, 1.2 mmol), and N,N-diisopropylethylamine (174 muL, 1 mmol) in n-butanol (10 mL) was refluxed at 130 C for 36 h. Then saturated NaHCO3 (2.5 mL) was added to neutralize the solution. The mixture was extracted with ethyl acetate, the organic layer was combined, dried over anhydrous Na2SO4 and concentrated. The crude product was purified by silica gel chromatography to afford 9 (242 mg, 65% yield). 1H NMR (400 MHz, DMSO-d6) delta: 11.90 (s, 1H), 9.62 (s, 1H), 7.92 (d, J = 7.9 Hz, 2H), 7.82 (s, 1H), 7.45 (d, J = 7.7 Hz, 2H), 6.19 (s, 1H), 5.85 (s, 1H), 4.55 (s, 2H), 3.83 (s, 3H), 2.15 (d, 3H); 13C NMR (100 MHz, DMSO-d6) delta: 166.1, 164.4, 161.7, 160.8, 148.1, 146.1, 138.1, 129.2, 129.1, 127.9, 127.2, 126.9, 95.4, 93.2, 51.9, 43.9, 10.6 ppm. HRMS (ESI-TOF): m/z calcd. for C17H18N6O2Cl, [M+H]+: 373.1174; found: 373.1143.

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; Luo, Yu; Deng, Yan-Qiu; Wang, Jing; Long, Zi-Jie; Tu, Zheng-Chao; Peng, Wei; Zhang, Ji-Quan; Liu, Quentin; Lu, Gui; European Journal of Medicinal Chemistry; vol. 78; (2014); p. 65 – 71;,
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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 120974-97-2 as follows. name: (E)-Methyl 2-(methoxyimino)-2-(o-tolyl)acetate

1.5 1 of 25% strength ammonia water are added to 120 g (0.5 mol) of methyl E-2-methoximino-2-(2-methylphenyl)-acetate in 1.5 l of methanol and the mixture is refluxed for 5 hours. The reaction mixture is then allowed to cool, concentrated to approximately 1l, stirred with water and extracted by shaking with ethyl acetate. The organic phase is washed with water, dried over sodium sulphate and concentrated in vacuo. The residue is stirred with diisopropyl ether, filtered off with suction and dried. 66.2 g (69% of theory) of E-2-methoximino-2-(2-methylphenyl)-acetamide of melting point 98-99 C. are obtained.

According to the analysis of related databases, 120974-97-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US6194464; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 57381-43-8, name is Methyl 2,5-dibromobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6Br2O2

General procedure: Method A:16,17 A two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar was charged with the 2-bromobenzoic acid (20mmol) and freshly distilled methanol (25mL). The solution was heated in a hot water bath, conc. H2SO4 (8mmol) was added slowly and the reaction mixture was refluxed for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the residue was partitioned between water (50mL) and diethyl ether (70mL). The organic layer was separated and washed with saturated NaHCO3 (2×50mL), water (50mL) and brine (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product thus obtained was purified by flash chromatography on silica gel to afford the alkyl-2-halobenzoate. (0023) In a two-necked round-bottomed flask equipped with a reflux condenser and a magnetic stir bar the alkyl 2-halobenzoate (22.5mmol) was dissolved in freshly distilled dry THF (30mL) under argon. The solution was cooled to 0°C using an ice bath and NaH (60percent in mineral oil, 15mmol) was added portionwise. After stirring for 15min a solution of the alkyl acetate (15mmol) in dry THF (30mL) was added dropwise to the reaction mixture at 0°C. The mixture was warmed up, stirred at room temperature for 2h and heated under reflux for 24h. After cooling to room temperature around half of the amount of the solvent was removed in vacuo and the reaction mixture was diluted with toluene (50mL). The resulting mixture was washed with 2N HCl (50mL), saturated NH4Cl (50mL), dried over anhydrous MgSO4 and the volatiles were removed under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford the alkyl 3-(2?-halophenyl)-3-oxo-propanoate 1.

The synthetic route of 57381-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Weischedel, Heike; Sudheendran, Kavitha; Mikhael, Alevtina; Conrad, Juergen; Frey, Wolfgang; Beifuss, Uwe; Tetrahedron; vol. 72; 24; (2016); p. 3454 – 3467;,
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These common heterocyclic compound, 57486-68-7, name is Methyl 2-chlorophenylacetate, 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. Product Details of 57486-68-7

To a stirred solution of 54 (300 mg, 1.75 mmol) and methyl 2-(2- chlorophenyl)acetate 55 (325 mg, 1.75 mmol) in dry DMA (4 mL), KF/AI2O3 (1800 mg, 40 wt %) was added and the reaction mixture was stirred at room temperature for 2 h. After completion the reaction mixture was filtered through celite and the residual solid was washed with DCM and filtrate was concentrated. The residue was purified by column chromatography using silica gel (20 % EtOAc/Hexane) to give 56 (400 mg, 75%) as white solid. lH NMR (400 MHz, CDCb) delta (ppm) 8.54 (s, 1H), 7.72 (s, 1H), 7.44-7.39 (m, 1H), 7.34-7.26 (m, 4H), 3.65 (s, 3H).

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

Reference:
Patent; UNIVERSITY OF HOUSTON SYSTEM; TRUSTEES OF TUFTS COLLEGE; CUNY, Gregory; NIKHAR, Sameer; DEGTEREV, Alexei; (78 pag.)WO2018/213219; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 103-25-3, name is Methyl 3-phenylpropionate, 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 103-25-3, Computed Properties of C10H12O2

In the 10mL single-mouth bottle,Nitrogen protection,82.1 mg (0.50 mmol) of compound 1e is added,2.5mL n-pentane,105.9 mg (2.25 mmol) deuterated ethanol (EtOD),16.0 mg (2.25 mmol) lithium block,Stir for 5 min at 0C.Rise to room temperatureThe reaction was quenched with 3.0 M aqueous hydrochloric acid.Add ether and saturated salt,59.0 mg of target compound 4a was obtained.Yield 85%.

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; China Agricultural University; An Jie; Lei Peng; Han Minhui; Ma Xiaodong; Wu Yufei; A Dila·adijiang; Ding Yuxuan; (15 pag.)CN107445798; (2017); A;,
Ester – Wikipedia,
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Synthetic Route of 369-26-6, 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. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a 40 mL reaction vessel was charged 8-chloro-N-(2-fluorobenzyl)-N-(2- hydroxyethyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamide (I-73) (0.10 mmol) and CH2Cl2 (10 mL) followed by the addition of commercial Dess-Martin Periodinane (Sigma- Aldrich, 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H-one, 0.20 mmol) and buffered with solid sodium bicarbonate (0.20 mmol). The milky white suspension was rapidly stirred for 2 hrs and then the reaction was then directly diluted with ethyl acetate (150 mL) and washed with water (3 x 15 mL). The resulting organic extract was concentrated to a residue (in vacuo) and used directly without delay or further manipulation. The residue was dissolved in 9:1 MeOH/AcOH (5 mL) and treated with methyl-3-amino benzoate (0.40 mmol). The resulting reaction was then stirred at room temperature for 30 mins. and then treated with sodium cyanoborohydride (1.0 mmol, portion-wise over 30 mins.) followed by stirring at room temperature for an additional 1 hr. The resulting reaction was diluted with ethyl acetate (150 mL) and washed with water (3 x 25 mL). The resulting organic extracts were concentrated in vacuo and then directly subjected to reverse phase chromatography using TFA-modified (0.05 percent) water/ACN (35 to 80 percent). All fractions were reduced to dryness under vacuum and subjected to a free base event using polymer immobilized carbonate (SPE-C03H Varian cartridge, 0.90 nominal load with MeOH mobilizer, 10 mL) to give methyl 3-((2-(8-chloro-N-(2- fluorobenzyl)-1-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamido)ethyl)amino) benzoate (63-lnt) as a white solid. 1H NMR (400 MHz, d4-MeOH): delta 7.48-7.19 (m, 8H), 7.03- 6.92 (3H), 7.18 (app d, J = 8.0 Hz, 1 H), 6.62 (app dt, J = 12.2, 8.0 Hz, 1 H), 5.30-5.20 (m, 2H), 4.83 (br s, 2H), 4.21 (t, J = 5.0 Hz, 2H), 3.85 (s, 3H), 3.74 (s, 3H), 3.38 (t, J = 5.0 Hz, 2H). Mixture of rotamers. MS (m/z): 549.2/551.2 (M+H)+(chlorine isotope pattern).

The synthetic route of Methyl 3-amino-4-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; CHIANELLI, Donatella; LIU, Xiaodong; MOLTENI, Valentina; NELSON, John; ROLAND, Jason; RUCKER, Paul; TULLY, David; WO2015/69666; (2015); A1;,
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