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. 3153-37-5, name is Methyl 4-chlorobutyrate, A new synthetic method of this compound is introduced below., COA of Formula: C5H9ClO2

EXAMPLE 1 Methods for the preparation of the compounds of the invention are disclosed in U.S. Pat. No. 6,147,250. The following is a method of producing Compound A. Probucol (5, 9.69 mmol) and methyl 4-chlorobutyrate (3.1 g. 1.4 eq) were stirred in DMF (15 mL) and potassium fluoride on alumina (7 g, 5 eq) was added. The mixture was stirred at room temperature under nitrogen for 20.5 hours. It was filtered, diluted with ethyl acetate (100 mL), washed with water and brine, dried over sodium sulfate, and evaporated. Chromatography (MPLC, 10% to 80% of dichloromethane in hexanes) gave 0.98 g of methyl 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyrate. Methyl 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyrate (0.95 g, obtained above) was dissolved in THI/MeOH/H2O (4:1;1, 15.4 mL) and lithium hydroxide hydrate (0.19 g) was added. The mixture was stirred at room temperature for four hours and then acidified with 0.3 N HCl. The mixture was poured into brine and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated to give 0.60 g of 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyric acid (Compound A) as a solid.

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; Edwards, David B.; Somers, Patricia K.; Glass, Mitchell; US2002/156022; (2002); A1;,
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Reference of 24812-90-6, A common heterocyclic compound, 24812-90-6, name is Methyl 3-amino-4-methoxybenzoate, molecular formula is C9H11NO3, 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.

Step 1: 4-Methoxy-3-(4-nitro-phenoxycarbonylamino)-benzoic acid methyl ester. To a stirred, cooled (0 C.) solution of methyl-3-amino-4-methoxy benzoate (5.0 g; 27.6 mmol) in methylene chloride (100 mL) was added pyridine (2.34 mL; 29 mmol) followed by 4 nitrophenyl chloroformate (5.8 g; 29 mmol). After stirring for 8 hours, the reaction was diluted with methylene chloride (100 mL), washed with IN hydrochloric acid (2*125 mL), 10% aqueous sodium carbonate (2*125 mL), brine (1*125 mL), then dried (MgSO4), and filtered. The filtered material was concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) followed by hexanes (700 mL). A precipitate formed which was filtered to yield an off white solid (80% yield).

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; Keegan, Kathleen S.; Kesicki, Edward A.; Gaudino, John Joseph; Cook, Adam Wade; Cowen, Scott Douglas; Burgess, Laurence Edward; US2003/69284; (2003); A1;,
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7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C6H6N2O4

General procedure: To a solution of diazo compound 1 (0.5 mmol) and alkynes (1.1 mmol) in toluene (2 mL) was added rhodium(II) pivalate (0.01 mmol). The reaction mixture was stirred at 60C for 0.5-5 h. The solvent was evaporated in rotary evaporator under reduced pressure to give the residue. The residue was purified by flash column chromatography on silica gel to give the product. 4.2.13. 2,4-Bis(4-(trifluoromethyl)phenyl)-6H-furo[2,3-b]pyran-6-one (5l). Reaction of 1 (85 mg, 0.5 mmol) and 4-ethynyl-alpha,alpha,alpha-trifluorotoluene (187 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 5l (106 mg, 50%) as a solid: mp 158-160 C; 1H NMR (300 MHz, CDCl3) delta 7.82 (2H, d, J=8.1 Hz), 7.76-7.73 (4H, m), 7.65 (2H, d, J=8.1 Hz), 6.94 (1H, s), 6.26 (1H, s); 13C NMR (75 MHz, CDCl3) delta 158.6, 152.1, 147.3, 138.4, 131.9, 128.2, 127.9, 126.4, 126.3, 126.3, 126.1, 126.0, 125.1, 123.7, 106.4, 102.4, 99.5; IR (KBr) 3125, 1728, 1616, 1528, 1325, 1127, 837, 672 cm-1; HRMS m/z (M+) calcd for C21H10F6O3: 424.0534. Found: 424.0532.

The synthetic route of 7270-63-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
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Reference of 344-14-9, The chemical industry reduces the impact on the environment during synthesis 344-14-9, name is Dimethyl 2-fluoromalonate, I believe this compound will play a more active role in future production and life.

General procedure: [Pd(C3H5)Cl]2 (0.004 mmol, 4 mol%), [6-(allyloxymethyl)-N-(2-((R)-((S)-1-(3,5-dimethoxyphenyl)propyl)sulfinyl)phenyl)picoli-namide] (6b, 0.008 mmol, 8 mol%), and (E)-1,3-disubstituted allyl acetates 7 (0.1 mmol) were dissolved in THF (2.0 mL) in a dry Schlenk tube filled with argon. The reaction mixture was stirred for 30 min at room temperature. Then Cs2CO3 (3.0 equiv) and dimethyl 2-fluoromalonate 8 (0.3 mmol, 3.0 equiv) were added. After the completion of the reaction monitoring by TLC, the crude reaction mixture was filtrated with celite and the solvent was removed under reduced pressure. The crude residue was purified by flash column chromatography (petroleum ether/ethyl acetate) to give the desired products 9.

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:
Article; Zhang, Min; Zhao, Mingzhu; Zheng, Purui; Zhang, Hongbo; Zhao, Xiaoming; Journal of Fluorine Chemistry; vol. 189; (2016); p. 13 – 21;,
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37466-90-3, name is Ethyl 3,4-diaminobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of Ethyl 3,4-diaminobenzoate

General procedure: The corresponding dianiline (1 eq.), the corresponding aromatic acid (1.1 eq.), HATU (1.1 eq.) and N,N-diisopropyl-ethylamine (2 eq.) in dichloromethane (2 mL/g) was stirred overnight at room temperature. The product was isolated as per specification.

The synthetic route of 37466-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elkins, Jonathan M.; Fala, Angela M.; Massirer, Katlin B.; Pennicott, Lewis E.; Reuillon, Tristan D.; Scott, Fiona; Ward, Simon E.; Bioorganic and medicinal chemistry letters; (2020);,
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Reference of 23426-63-3, 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. 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, This compound has unique chemical properties. The synthetic route is as follows.

A 3 neck round bottom flask equipped with a mechanical stirrer, thermometer, condenser and nitrogen bubbler, was charged with malononitrile (251 g, 3.80 moles) and THF (2 liters). t-BuOK (1 M THF, 3.80 L, 3.80 moles) was then added. The mixture was stirred at 50C for 0.5 h. Methyl 2-bromoisobutyrate (688 g, 3.80 moles) was added and the reaction mixture was stirred overnight at 50C. The reaction was partitioned between aqueous 1 N HCI and EtOAc. The organic phase was washed with brine, dried over anhyd. magnesium sulfate, filtered, and concentrated to afford the title compound. H NMR (400 MHz, CD3CN): delta 4.35 (1 H, s) 3.73 (3H, s), 1.43 (6H, s).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-2-methylpropanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GARFUNKLE, Joie; ORNOSKI, Olga; PARKER, Dann, L., Jr.; RAGHAVAN, Subharekha; XU, Libo; (88 pag.)WO2016/191334; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2033-24-1, name is 2,2-Dimethyl-1,3-dioxane-4,6-dione, 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 2033-24-1, category: esters-buliding-blocks

2,4,5-trifluorophenylacetic acid (30 g), tetrahydrofuran (360 ml_), 1 ,1 -carbonyl diimidazole (25.5 g) at about 5O0C, and meldrums acid (22.7 g) are combined. The mixture is stirred for about five hours at the same temperature. The reaction mass is then cooled to about 3O0C. Isopropyl acetate (180 ml_) and water (180 ml_) are added and stirred for about 30 minutes. The reaction mass is cooled to about O0C and pH is adjusted to about 2.4 using 36% aqueous hydrochloric acid. The organic layer is separated, washed with 0.1 N aqueous hydrochloric acid and distilled off completely. To the residue obtained, n-heptane (140 ml_) and isopropyl acetate (70 ml_) are charged at about 3O0C and stirred at about O0C for about 90 minutes. The separated solid is filtered and washed with a mixture of n-heptane (20 ml_) and isopropyl acetate (10 ml_). The wet cake is dried at about 5O0C for about 4 hours to afford the title compound. (Yield: 60.1 %; purity by HPLC: 98.0%)

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; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES, INC.; WO2009/85990; (2009); 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 4341-76-8 as follows. Product Details of 4341-76-8

General procedure: In a two neck rbf was stirred a mixture of Pd(OAc)2 (275 mg,1.22 mmol) and TDMPP (540 mg, 1.22 mmol) in benzene (30 ml)for 15 min at rt under nitrogen. To this mixture was added ethyl-2-butynoate 7 (2.84 ml, 24.48 mmol) and the resulting mixturewas further stirred for 10 min at rt. Next, ethynylbenzene 4a(2.50 g, 24.48 mmol) was added to this solution and the mixturewas stirred for 5-10 min until reaction was completed. Theworkup of reaction was performed by evaporating the solvent invacuum followed by column chromatography (Hexane:EtOAc = 100:1) to give the desired compound 8a (2.62 g);

According to the analysis of related databases, 4341-76-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Singh, Sarbjit; Goo, Ja-Il; Noh, Hyojin; Lee, Sung Jae; Kim, Myoung Woo; Park, Hyejun; Jalani, Hitesh B.; Lee, Kyeong; Kim, Chunsook; Kim, Won-Ki; Ju, Chung; Choi, Yongseok; Bioorganic and Medicinal Chemistry; vol. 25; 4; (2017); p. 1394 – 1405;,
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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 10259-22-0 as follows. Recommanded Product: Ethyl 3-methoxybenzoate

General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)

According to the analysis of related databases, 10259-22-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pramanick, Pranab Kumar; Hou, Zhen-Lin; Yao, Bo; Tetrahedron; vol. 73; 50; (2017); p. 7105 – 7114;,
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Electric Literature of 2905-65-9, 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. 2905-65-9, name is Methyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Substituted benzoic acid (1.0 mmol) was dissolved in thionylchloride and refluxed for 2 h, then the solvent was removed underreduced pressure to obtain the white solid. The white solid in methanol was added concentrated sulfuric acid (1 mL) and themixture was refluxed for 4 h, the solvent was removed to obtaincrude solid. The crude solid was extracted with ethyl acetate andwater. The solvents were evaporated to afford the pure product.Finally, the pure product was dissolved in ethanol, and the hydrazinehydrate was added. The mixture was refluxed for 9 h, and thesolvent was removed

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

Reference:
Article; Lian, Zhi-Min; Sun, Juan; Zhu, Hai-Liang; Journal of Molecular Structure; vol. 1117; (2016); p. 8 – 16;,
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