Month: February 2021

Reference of 32122-09-1, 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. 32122-09-1 name is Ethyl 2-(benzyloxy)acetate, 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.

EXAMPLE 83 Preparation of 2-benzyloxyacetyl-gamma-butyrolactone: A solution of 10.6 ml of diisopropylamine in 75 ml of tetrahydrofuran was chilled to -70 C., and 46 ml of a 1.6N hexane solution of n-butyllithium were added dropwise to the solution. After completion of the addition, the mixture was stirred for 15 minutes, and a solution of 54.8 g of gamma-butyrolactone in 50 ml of tetrahydrofuran was added dropwise over 55 minutes, and the mixture was stirred for 50 minutes. Further, a solution of 14.75 g of ethyl benzyloxyacetate in 50 ml of tetrahydrofuran was added, and the resultant mixture was stirred for 2.5 hours at -60 to -50 C. 5N hydrochloric acid was then added so as not to exceed 20 C. to adjust the pH of the mixture to 1-2. Ethyl acetate was added to the reaction system, and the resultant mixture was washed with a saturated saline solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The thus-obtained crude product was subjected to column chromatography on silica gel (elution solvent: hexane:ethyl acetate=3:1?2:1?1:1) to obtain 13.01 g (yield: 87.2%) of the intended product as a colorless oil. 1 H-NMR (CDCl3, ppm): 2.30(1H,m), 2.75(1H,m), 3.88(1H,m), 4.27-4.47(4H,m), 4.68(2H,s), 7.29-7.38(5H,m).

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

Reference:
Patent; Pola Chemical Industries, Inc.; US5942515; (1999); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 106-32-1, A common heterocyclic compound, 106-32-1, name is Ethyl octanoate, molecular formula is C10H20O2, 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.

Dissolve 0.155037g (0.00189mol, 0.02eq) of sodium acetate and 0.100161g (0.000945mol, 0.01eq) of sodium carbonate in 5mL of water, add 100mL of ethanol, and add the colorless liquid product obtained in step (a) (containing 0.0945mol of compound 2. Based on 1.0eq), react at 40 C for 2.5 hours. During the reaction, 6.2676g (0.094878mol, 1.004eq) hydroxylamine aqueous solution was added dropwise. After the reaction was completed, it was filtered and distilled under reduced pressure to remove ethanol. After adding 100 mL of water, the temperature was lowered to 0 C, and then slowly added dropwise sulfuric acid to adjust the pH to 3.5 to precipitate a white solid, which was filtered, washed with water, and dried to obtain 14.415 g of a white solid. Based on octanoyl hydroxamic acid, the white The purity of the solid was 99.9%, and the yield was 95.7%.

The synthetic route of 106-32-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Heze Xin Eastern Countries Rihua Technology Co., Ltd.; Xue Tianhui; Chen Xiaohui; Chen Kun; Qin Lijin; (12 pag.)CN110845367; (2020); A;,
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. 34529-06-1, name is Dimethyl 3-aminophthalate, A new synthetic method of this compound is introduced below., Formula: C10H11NO4

Example 7 3-(3-Ethoxy-4-methoxy-phenyl)-3-(4-isobutylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionitrile To a mixture of dimethyl-3-aminophthalic ester (0.75 g, 3.6 mmol), 3-methyl-butyraldehyde (0.36 mL, 4.0 mmol), acetic acid (1.3 mL, 23 mmol) in 1,2-dichloroethane (30 mL), was added sodium triacetoxyborohydride (1.5 g, 7.2 mmol) at room temperature. After 30 minutes, the mixture was extracted with methylene chloride (30 mL) and water (30 mL). The organic layer was washed with sodium hydrogen carbonate (sat. 30 mL). The solvent was removed in vacuo to give a yellow oil. To the oil in methanol (5 mL), was added sodium hydroxide (10 N, 1.5 mL), and kept at room temperature overnight. To the mixture, was added HCl (12 N, 1.3 mL). The solvent was removed in vacuo to give a solid. The solid was dissolved in pyridine (10 mL), and 3-amino-3-(3-ethoxy-4-methoxy-phenyl)-propionitrile (1.0 g, 3.6 mmol) was added to the solution. The solution was heated to reflux for 2 days. The solvent was removed in vacuo to give an oil. The oil was extracted with ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with water (50 mL), HCl (1N, 2*50 muL), water (50 mL), sodium hydrogen carbonate (sat, 2*50 mL), and brine (50 mL), and dried over MgSO4. Filtration and removal of solvent in vacuo gave an oil. The oil was purified by column chromatography (Silca Gel, 1:3 EtOAc:hexanes) to give 3-(3-ethoxy-4-methoxy-phenyl)-3-(4-isobutylamino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionitrile as a yellow solid (700 mg, 46% yield): mp, 12-123 C.; 1H NMR (CDCl3) delta 1.01 (d, J=7 Hz, 6H, 2CH3), 1.45 (t, J=7 Hz, 3H, CH3), 1.88-1.99 (m, 1H, CH), 3.07 (t, J=6 Hz, 2H, CH2), 3.27 (dd, J=7, 17 Hz, 1H, CHH), 3.76 (dd, J=10, 17 Hz, 1H, CHH), 3.84 (s, 3H, CH3), 4.09 (q, J=7 Hz, 2H, CH2), 5.55 (dd, J=7, 10 Hz, 1H, NCH), 6.37 (t, J=6 Hz, 1H, Ar), 6.81-6.86 (m, 2H, Ar), 7.01-7.06 (m, 3H, Ar), 7.44 (t, J=8 Hz, 1H, Ar); 13C NMR (CDCl3) delta 14.69, 20.26, 21.29, 28.27, 50.31, 50.63, 55.95, 64.49, 109.63, 111.10, 111.42, 112.22, 116.58, 117.09, 119.96, 129.55, 132.33, 135.93, 147.14, 148.53, 149.66, 168.18. Analy. Calculated for C24H27N3O4: C, 68.39; H, 6.46; N, 9.97. Found: C, 68.32; H, 6.39; N, 9.95.

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; Muller, George W.; Man, Hon-Wah; US2006/84815; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14064-10-9, name is Diethyl 2-chloromalonate, 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 14064-10-9, Application In Synthesis of Diethyl 2-chloromalonate

3-Bromobenzenecarbothioamide (1.00 g, 4.62 mmol) and diethyl chloropropanedioate (1.0 mL, 6.0 mmol) were dissolved in dioxane (35 mL). The mixture was heated at 80¡ãC and stirred overnight, whereupon the solvent was removed under vacuum. Ethyl 2-(3-bromophenyl)-4-hydroxy-1 ,3-thiazole-5-carboxylate was obtained as a yellow solid (1.09 g, 72percent) by trituration in acetonitrile. An oven-dried Schlenk tube equipped with a magnetic stir bar was charged with 1.5 mL of an aqueous solution of K2CO3 (2M, 3.0 mmol), tetrakis(triphenylphosphine)palladium(0) (140 mg, 0.121 mmol) and toluene (3 mL). The tube was capped with a rubber septum and immersed in an oil bath at 80 ¡ãC for 30 min. Ethyl 2-(3′-bromophenyl)-4-hydroxy-1 ,3- thiazole-5-carboxylate (188 mg, 0.575 mmol) and 2-trifluoromethyl-phenylboronic acid (218 mg, 1.15 mmol) were then added, and the reaction mixture stirred at 80¡ãC. Upon complete consumption of the starting material (12 h), as judged by thin-layer chromatography analysis, the reaction mixture was filtered on a celite pad. The filtrate was diluted with ethyl acetate, and extracted with water. The organic layers were further washed with brine and dried over sodium sulfate. The product was isolated by column chromatography (hexanes/EtOAc) as a yellow solid (56 mg, 25percent). 1H-NMR (DMSO-cie) delta (ppm): 10.82 (br s, 1 H), 7.96 (d, 2H, J=8.11), 7.86 (d, 2H, J=7.57), 7.78-7.73 (m, 1 H), 7.67-7.62 (m, 1 H), 7.47-7.41 (m, 2H), 4.16 (q, 2H, J=7.03), 1.24 (t, 3H, J=7.03).

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; DOMPE’ S.P.A.; MORICONI, Alessio; BIANCHINI, Gianluca; COLAGIOIA, Sandro; BRANDOLINI, Laura; ARAMINI, Andrea; LIBERATI, Chiara; BOVOLENTA, Silvia; WO2013/92711; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 106-32-1, A common heterocyclic compound, 106-32-1, name is Ethyl octanoate, molecular formula is C10H20O2, 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: Ester, ruthenium catalyst , metal alkoxide co-catalyst (used as a solid or some alcoholic solution) and optionally solvent (see Table 1) were loaded altogether in an 100 mL or 1L autoclave equipped with a mechanical stirring device, pressure and internal temperature sensors and a heating/cooling system for internal temperature regulation. Sealed autoclave was then purged under stirring with nitrogen (3 times 5 bars) and hydrogen (3 times 5 bars) before being pressurized to required hydrogen pressure via an hydrogen tank equipped with a way out pressure regulator and also an internal pressure sensor to follow and determine hydrogen consumption. Reaction mixture was then heated to required temperature and hydrogen pressure into the autoclave was maintained to the desired value during the whole reaction. Upon reaction completion also determined by GC analysis with complete disappearance of both starting material and mixed ester coming from transesterification reaction with product and eventually with metal alkoxide co-catalyst and/or alcoholic solvent, autoclave was then cooled down to 25 C. It was then depressurized and purged with nitrogen (3 times 5 bars) and reaction mixture was then transferred to a round-bottomed flask and lights compounds were removed under vacuum. Crude product was then flash distilled in order to determine the quantity of residues formed during the reaction and yield was calculated based on GC purity of distilled product.

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; FIRMENICH SA; DUPAU, Philippe; BONOMO, Lucia; KERMORVAN, Laurent; HALDIMANN SANCHEZ, Murielle; (46 pag.)WO2019/175158; (2019); A1;,
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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., Safety of Trimethyl methanetricarboxylate

Step 3; methyl 9-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-7-methyl-2-oxo-2,5,6,7- tetrahydro-lH-benzo [b] pyrido [2,3-d] azepine-3-carboxylate Crude N-(8-chloro-l-methyl-3,4-dihydro-lH-benzo[b]azepin-5(2H)-ylidene)-l-(2,4- dimethoxyphenyl)methanamine (690 mg, 1.95 mmol) and trimethyl methanetricarboxylate (631 mg, 3.32 mmol) were mixed together in Pl^O (4.0 mL). With stirring, the mixture was placed into a pre-heated heat block at 210 C and heated for 10 minutes under a blanket of Argon. The reaction mixture was cooled to room temperature and was filtered directly on a silica cartridge. The product was purified by column chromatography (100% hexanes followed by EtOAc in hexanes 0 to 85% gradient) to provide the desired product (289 mg, 31%, two steps) as an off-white foam which was used directly in the next step. LC-MS 483.9 [M-H]”, 485.8 [M+H]+, RT 1.53 min.

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; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 939-18-4, name is 3-Bromo-2H-chromen-2-one belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 939-18-4

General procedure: Typically, (hetero)aryl bromide (1.0 mmol), thiazole derivatives(2.0 mmol), Pd-PEPPSI complexes (0.01e0.5 mol%), base (2 mmol),acid additive (0.3 mmol), and 3mL of DMAc solvent were addedinto a parallel reactor. After heating at 130 C for 4 h, the resultingmixture was cooled to room temperature. Subsequently, 25mL ofwater and 20 mL of dichloromethane were added into the reactor,and the mixture was stirred for another several minutes, followedby extraction three times with dichloromethane (3 x 5 mL). Theorganic layer was then combined, dried over anhydrous sodiumsulfate, filtered, and evaporated under reduced pressure to give thecrude products. The crude products were then purified by silica-gelcolumn chromatography using petroleum etheredichloromethane(15/1) as the eluent. The obtained pure products were characterizedby 1H NMR and 13C NMR spectroscopy, and the spectra can be foundin the Supporting Information. And the isolated yields of productswere obtained based on the amounts of (hetero)aryl bromides.

The synthetic route of 939-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Bei-Bei; Lan, Xiao-Bing; Shen, Dong-Sheng; Liu, Feng-Shou; Xu, Chang; Journal of Organometallic Chemistry; vol. 897; (2019); p. 13 – 22;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 22223-49-0, name is Methyl 2-amino-3-methylbenzoate, 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 22223-49-0, HPLC of Formula: C9H11NO2

N-Bromosuccinimide (38.5 g, 216 mmol) was added to a mixture consisting of methyl 2-amino-3-methylbenzoate (32.4 g, 196 mmol, Intermediate 89: step a) and dichloromethane (300 mL). The resultant reaction mixture was stirred at room temperature for 16 hours before it was poured into water (200 mL) and the aqueous phase was extracted with dichloromethane (200 mL*3). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to afford the title compound.

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; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1559-02-0, These common heterocyclic compound, 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, 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 mixture of diethyl 1 ,1-cyclopropanedicarboxylate (10.0 g, 53.7 mmol) in ethanol (70 mL) and water (35 mL) was added sodium hydroxide (2.1 g, 53.7 mmol). The reaction was stirred at 25 C for 16 h and diluted with ethyl acetate (60 mL). The organic layer was discarded. The aqueous phase was adjusted to pH = 3 by addition of aqueous hydrochloric acid (4 M). The mixture was extracted with ethyl acetate (3 x 80 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate and concentrated under reduced pressure to give crude 1- ethoxycarbonylcyclopropanecarboxylic acid (6.6 g, 78%) as a colorless oil. NMR (400MHz, CDCl3) delta 12.86 (br s, 1H), 4.31 – 4.17 (m, 2H), 1.87 – 1.81 (m, 2H), 1.77 – 1.69 (m, 2H), 1.32 – 1.24

The synthetic route of 1559-02-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

206548-14-3, name is Methyl 2-amino-5-bromo-3-methylbenzoate, 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. Recommanded Product: 206548-14-3

5-Bromo-2-(4-fluoro-benzenesulfonylamino)-3-methyl-benzoic acid By following the procedure of Example 134 the product of Example 133 and 4-fluorobenzenesulfonyl chloride provides 5-bromo-2-(4-fluoro-benzenesulfonylamino)-3-methyl-benzoic acid as a yellow solid in 36% yield. Electrospray Mass Spec: 386.0 (M-H)-

The synthetic route of 206548-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; EP938471; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics