Category: esters-buliding-blocks

Synthetic Route of 15568-85-1, 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. 15568-85-1 name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, 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.

A solution of 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (7.0g,37.7mmol) and 2-methoxypyridin-4-amine (3.6g, 29.0mmol) disolved in i-PrOH(50mL) was refluxed at 100C for 1 hour, then the reaction solution was cooled toroom temperature to give crystalline solid which was filtered, washed with i-PrOHand diethyl ether to affor the compound 11 as a yellow crystalline solid (5.2g, 65%).1H NMR (400 MHz, Chloroform-d) delta 11.08 (d, J = 14.0 Hz, 1H), 8.66 (d, J = 14.0Hz, 1H), 8.17 (d, J = 5.7 Hz, 1H), 6.75 (dd, J = 5.7, 1.8 Hz, 1H), 6.55 (d, J = 1.8 Hz,1H), 3.95 (s, 3H), 1.75 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, and friends who are interested can also refer to it.

Reference:
Article; Cheng, Yu; Shen, Jian; Peng, Run-Ze; Wang, Gui-Feng; Zuo, Jian-Ping; Long, Ya-Qiu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 12; (2016); p. 2900 – 2906;,
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Related Products of 46004-37-9, The chemical industry reduces the impact on the environment during synthesis 46004-37-9, name is Methyl 4-amino-2-chlorobenzoate, I believe this compound will play a more active role in future production and life.

To a suspension of methyl 4-amino-2- chlorobenzoate (20.0 g, 107.75 mmol) and CaCO3 (21.58 g, 215.5 mmol) in MeOH (216 mL) was added a solution of iodine monochloride (20.0 g, 123.2 mmol) in CH2CI2 (102 mL). The resulting reaction mixture was stirred at room temperature for 5 h, and quenched by adding cooled water (700 mL) and ethyl acetate (700 mL). It was filtered through celite, the filtrate was treated with 300 mL of 10% sodium thiosulfate, partitioned, and the aqueous layer was extracted with ethyl acetate (400 mL). The combined organic layers were washed with 10% sodium thiosulfate (2x), and brine. The organic layer was dried over Mg504, and concentrated to dryness under vacuum. The residue was adsorbed in silica gel, loaded into flash column which was eluted with 5, 7.5, and 10% ethyl acetate/toluene to afford 17.0 g of title compound as a yellow solid. 1H NMR (400 MHz, CDCI3): 6 8.26 (s, 1H),6.75 (s, 1H), 4.52 (bs, 1H), 3.87 (s, 3H). LCMS (M+1) 312.0, 314.0.

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 4-amino-2-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING / MCGILL UNIVERSITY; TREMBLAY, Michel L.; PENAFUERTE, Claudia; FELDHAMMER, Matthew; ZOGOPOULOS, George; BLACK, Cameron; CRANE, Sheldon; TRUONG, Vouy-Linh; KENNEDY, Brian; WO2015/127548; (2015); A1;,
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Electric Literature of 35180-01-9, These common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl 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.

To a stirred solution of 5-((4′-isopropyl-[l,r-biphenyl]-4-yl)oxy)-l-(4-methoxy benzyl)-lH-l, 2, 3-tri azole-4- carboxylic acid 23 (330 mg, 0.744 mmol) in DMA (3.0 mL) was added potassium carbonate (77 mg, 0.558 mmol), stirred at rt for 30 min. To the resultant suspension was added neat chloromethyl isopropyl carbonate (170 mg, 1.12 mmol), heated for 6 h at 50 C until clear solution, cooled to rt, acidified with aq. 10% citric acid, extracted with ethyl acetate (30 mL), washed with brine, dried (Na2S04), and concentrated. The residue was purified on 40 g SiC cartridge using a gradient of ethyl acetate in hexanes (0 to 50%) as eluant to afford the title compound (350 mg, 84.1%) as colorless gum. Rf = 0.19 (20% EtOAc in hexanes). NMR (400 MHz, Chloroform-d) d 7.50 – 7.41 (m, 4H), 7.33 – 7.24 (m, 2H), 7.24 – 7.16 (m, 2H), 6.85 – 6.74 (m, 4H), 5.79 (s, 2H), 5.36 (s, 2H), 4.79 (hept, J = 6.3 Hz, 1H), 3.74 (s, 3H), 2.95 (hept, J = 6.9 Hz, 1H), 1.29 (d, J = 7.0 Hz, 6H), 1.21 (d, J = 6.3 Hz, 6H). MS: ES+ 560.25 (M+l).

The synthetic route of 35180-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORFAN BIOTECH INC.; MAAG, Hans; FERNANDES, Miguel Xavier; ZAMBONI, Robert; AKBARIROMANI, Elham; BEAULIEU, Marc-Andre; LEBLANC, Yves; THAKUR, Pallavi; (157 pag.)WO2020/10309; (2020); 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. 454-31-9, name is Ethyl 2,2-difluoroacetate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2,2-difluoroacetate

To a cold (-78 0C) stirred solution of 1,4-dibromobenzene (86.4 g, 366 mmol) in tetrahydrofuran (800 mL) was added n-butyllithium (228 mL, 1.6 M in hexanes, 366 mmol). The mixture was stirred at -78 0C for 30 min and ethyl difluoroacetate (50 g, 402 mmol) was added over 2 min. The mixture was stirred at -78 C for 1 h. The reaction was quenched with 1 N hydrochloric acid (250 mL) and allowed to attain room temperature. Methyl tert-butyl ether (250 mL) was added and the layers were separated. The organic layer was washed with brine (100 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was distilled under vacuum to give the difluoroketone as a white glassy solid which was used in the next step.

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; MERCK FROSST CANADA LTD.; WO2009/70873; (2009); A1;,
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50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, 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. Formula: C9H11NO3

To a solution of compound 34 (4.0 g, 0.02 mol) in DCM(200 mL) was added bromine (1.36 mL, 0.02 mol). Themixture was stirred at room temperature for 20 h. It wasdiluted with saturated sodium hydrogen sulfite (50 mL) andthe aqueous solution was extracted with DCM. The combinedorganic layers were washed with brine, dried overNa2SO4 and filtered. The residue was purified by silica gelcolumn chromatography eluting with PE/EA to give whitepowder 35 (4.71 g, 82.06%). 35: 1H NMR delta (400 MHz,CDCl3) 8.04 (s, 1H), 6.14 (s, 1H), 5.87 (s, 2H), 3.89 (s, 3H),3.87 (s, 3H).

The synthetic route of 50413-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yi, Jingyu; Du, Guoxin; Zhao, Yuanyuan; Zhang, Liuqiang; Li, Bo; Zhu, Weiliang; Huang, Cheng; Li, Yiming; Guo, Fujiang; Medicinal Chemistry Research; vol. 27; 7; (2018); p. 1851 – 1862;,
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4131-74-2, name is Dimethyl 3,3-Thiodipropionate, 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. name: Dimethyl 3,3-Thiodipropionate

2.7098 g of NaH (60%) was added to 250 ml of dry three-necked flask,40 ml of anhydrous tetrahydrofuran (THF) was added,Stirred at room temperature for 10 min,A solution of dimethyl 3,3′-thiodipropionate (10.1015 g)In THF (30 ml) was added and heated to reflux,About 1h drops finished,After adding 10mlTHF rinse the dropping funnel,Continue to return after 1h,The reaction was stopped and allowed to cool to room temperature.The reaction solution was adjusted to a pH of 6 to 7 with 2% dilute hydrochloric acid and then extracted with dichloromethane (30 ml * 3)The layers were washed with saturated sodium chloride solution and the organic layer was collected and washed with sufficient anhydrous sodium sulfate and filtered. The filtrate was filteredThe solvent was removed by evaporation to give 7.5639 g of a yellow oily liquid,4-oxo-tetrahydro-2H-thiopyran-3-carboxylic acid methyl ester (II)Yield 88.7%.

The synthetic route of 4131-74-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangxi Science and Technology Normal University; Zhu Wufu; Zheng Pengwu; Sun Chengyu; Tang Qidong; Chen Chen; Lei Fei; Wu Chunjiang; Tu Yuanbiao; Ouyang Yiqiang; (42 pag.)CN105153190; (2017); B;,
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Adding a certain compound to certain chemical reactions, such as: 5164-76-1, name is Dimethyl pent-2-enedioate, 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 5164-76-1, COA of Formula: C7H10O4

General procedure: The crude aryl diazonium tosylate 9 thus obtained was dissolved or suspended in MeOH (30 mL). Dimethyl glutaconate (1.45 mL, 10.0 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol) were successively added while stirring. After stirring at r.t. for 15 h, the mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (40 mL) and H2O (25 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was briefly fractionated on SiO2 using CH2Cl2 or CH2Cl2- acetone (5:1) as eluent. Fractions containing arylation product were pooled and concentrated to give compound 10 of at least 90% purity (according to 1H NMR analysis). It was used in the next step without further purification.

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:
Article; Dar’In, Dmitry; Kantin, Grigory; Bakulina, Olga; ?alubovskis, Raivis; Krasavin, Mikhail; Synthesis; vol. 51; 10; (2019); p. 2230 – 2236;,
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Adding a certain compound to certain chemical reactions, such as: 927-68-4, name is 2-Bromoethyl acetate, 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 927-68-4, Recommanded Product: 2-Bromoethyl acetate

(R)-7-chloro-N-(piperidin-3 -yl)-4-(trifluoromethyl)benzo[b]thiophene-2-carboxamide (TFA salt, 95 mg, 0.20 mmol), Nal (50 mg, 0.33 mmol), K2C03 (180 mg, 1.30 mmole), 2- bromoethyl acetate (32 uL, 0.29 mmol) and DMF (2 mL) were added into a reaction flask, and stirred at room temperature overnight. The mixture was dissolved in ethyl acetate (20 mL) and water (5 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2x). The ethyl acetate layer was concentrated in vacuo and chromatographed on silica gel using hexanes and ethyl acetate to give title compound (50 mg, 0.11 mmol, 56%). ?H NMR (CD3OD, 400 MHz) 8.34 (s, 1H), 7.83 (dd, IN, J 0.4, 8.0 Hz), 7.68 (dd, 1H, J?0.4, 8.0 Hz), 4.50 (m, 2H), 4.38 (m, 1H), 3.73 (m, 1H), 3.56 (m, IH), 3.32 (m, 2H),3.02 (m, 2H), 2.14 (m, 5H), 2.00 (m, 2H), 1.79 (m, 2H). LCMS (ES) 449, 451 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromoethyl acetate, and friends who are interested can also refer to it.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; ICAHN SCHOOL OF MEDICINE AT MONT SINAI; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; KAMENECKA, Theodore, M.; KENNY, Paul; LINDSTROM, Jon, M.; WANG, Jingyi; JIN, Zhuang; DOEBELIN, Christelle; (95 pag.)WO2016/191366; (2016); A1;,
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Electric Literature of 22223-49-0, The chemical industry reduces the impact on the environment during synthesis 22223-49-0, name is Methyl 2-amino-3-methylbenzoate, I believe this compound will play a more active role in future production and life.

Example 64 – Preparation of methyl 3-methyl-N-(6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl)anthranilate Methyl 3-methylanthranilate (2.1 g, 13 mmol) was dissolved in 4 ml pyridine and 6-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride was added. After a mild exothermic reaction subsided the reaction mixture was stirred at 50C for 24 hours. The pyridine was removed by evaporation at reduced pressure and the residue was treated with in 10% aqueous sodium bicarbonate. Insouble material was collected by filtration, washed with ether and dried to yield 2.9 (63%) of the desired product as a solid, mp 198.5-205C. An analytical sample was prepared by recrystallization from ethanol to yield a crystalline solid, mp 208.5-210.5C. IR and 1H NMR spectra were in agreement with the assigned structure.

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 2-amino-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE DOW CHEMICAL COMPANY; EP142152; (1991); B1;,
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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. 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

59.1) tert-butyl 2-methyl-2-(10H-phenothiazin-2-yloxy)propanoate: 1.93 g (3 eq.) of K2CO3 is added to a solution of 1 g (4.6 mmol) of intermediate 21.1 in 10 ml of DMF. The reaction mixture was heated to 60 C. before the addition of 1.73 ml (2 eq.) of tert-butyl 2-bromoisobutyrate. The mixture is then taken to 110 C. and stirring is maintained at this temperature for 6 hours. After returning to 20 C., the mixture is poured into 100 ml of water and the product is extracted using twice 100 ml of ethyl acetate. The organic solution is finally washed with 100 ml of salt water, dried over sodium sulphate, filtered and concentrated to dryness under vacuum. The evaporation residue is purified on a silica column, eluent: ethyl acetate/heptane (1/9). 450 mg of a pale pink solid is obtained with a yield of 28%. Melting point: 138-140 C.

The synthetic route of 23877-12-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Auvin, Serge; Chabrier De Lassauniere, Pierre-Etienne; US2005/222045; (2005); A1;,
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