Category: esters-buliding-blocks

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. 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 139102-34-4

1.936 kg (6.22 mol) of a 65% Red-Al solution in toluene were charged with 1.25 l of toluene at -5 C. To this solution was added 0.66 kg (6.59 mol) of 1-methylpiperazine, which was rinsed in with 150 ml of toluene, keeping the temperature between -7 and -5 C. The mixture was then left to stir at 0 C. for 30 minutes. This solution was then added to a solution of 1.261 kg (5.147 mol) of methyl 4-bromo-2-methoxybenzoate (XV), dissolved in 4 l of toluene, keeping the temperature at -8 to 0 C. After rinsing in twice with 0.7 l of toluene, the mixture was then stirred at 0 C. for 1.5 hours. For the work-up, the solution was added to cold aqueous sulphuric acid at 0 C. (12.5 l of water+1.4 kg of conc. sulphuric acid). The temperature should increase at maximum to 10 C. (slow addition). The pH was adjusted to pH 1, if necessary, by addition of further sulphuric acid. The organic phase was separated off and the aqueous phase was extracted with 7.6 l of toluene. The combined organic phases were washed with 5.1 l of water and then substantially concentrated and the residue taken up in 10 l of DMF. The solution was again concentrated to a volume of about 5 l. Determination of the content by evaporation of a portion resulted in a converted yield of 1.041 kg (94.1% of theory). The solution was used directly in the subsequent stage. HPLC method A: RT about 12.1 mm. MS (Elpos): mlz=162 [M+H]. 1H NMR (CDC13, 400MHz): oe=3.93 (3H, s), 7.17 (2H, m), 7.68 (1H, d), 10.40 (1H, s)

The synthetic route of 139102-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; PLATZEK, Johannes; (30 pag.)US2018/244670; (2018); A1;,
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Some common heterocyclic compound, 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, molecular formula is C13H27NO5, 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. 252881-74-6

In a solution of tert-butyl 3- (2- (2- (2-aminoethoxy) ethoxy) ethoxy) propanoate (6.00 g, 21.64 mmol) and 3, 3′- ( (oxybis (ethane-2, 1-diyl) ) bis (oxy) ) dipropanoic acid (21.01 g, 84.00 mmol) in DMA (200 ml) were added EDC (18.00 g, 93.75 mmol) and DIPEA (5.00 g, 38.75 mmol) . The mixture was stirred overnight, then concentrated and purified by SiO 2 column chromatography (MeOH: CH 2Cl 2 = 1: 12 to 1: 5) to give the title compound as a white oil (9.15 g, 86%yield) . ESI m/z: calcd for C 23H 44NO 11 [M+H] +: 510.28, found: 510.55.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 252881-74-6, its application will become more common.

Reference:
Patent; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; ZHUO, Xiaotao; YANG, Qingliang; ZHAO, Linyao; HUANG, Yuanyuan; YE, Hangbo; YANG, Chengyu; LEI, Jun; GAI, Shun; GUO, Huihui; JIA, Junxiang; BAI, Lu; XIE, Hongsheng; ZHOU, Xiaomai; GUO, Zhixiang; LI, Wenjun; CAO, Mingjun; ZHENG, Jun; YE, Zhichang; YANG, Yanlei; (325 pag.)WO2020/6722; (2020); A1;,
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Ester – an overview | ScienceDirect Topics

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. 37466-90-3 name is Ethyl 3,4-diaminobenzoate, 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. 37466-90-3

General procedure: Compound 3 (10 mmol) was dissolved in ethylene glycol (50 mL) andthen compound 2 (10 mmol) and a small amount of polyphosphoricacid were added to the stirred solution which was then refluxed forseveral hours (the reaction was monitored by TLC). On completion ofthe reaction, the mixture was poured into ice water. The solution wastreated with 30% sodium hydroxide to slight alkalinity (pH = 9). Theprecipitated solid was filtered off, recrystallised from ethanol anddried in vacuo to give compound 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3,4-diaminobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Wang, Xinying; Liu, Yizhou; Xu, Juan; Jiang, Fanwei; Kang, Congmin; Journal of Chemical Research; vol. 40; 10; (2016); p. 588 – 590;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

25597-16-4, 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. 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[1051] A mixture of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (1.40 g, 6.51 mmole), K2C03 (1. 80 G, 13.02 mmole), triethylamine (2.63 g, 26.05 mmole), and ethyl 4,4, 4- trifluorocrotonate (4.38 g, 26.05 mmole) in anhydrous DMSO (5.0 mL) was heated to 90 C under a dry N2 atmosphere for 18 hrs. The contents were poured into 2.4 N HCL (50 ml) and extracted with EtOAc (2 X 100 mL). The combined extracts were washed with brine (100 mL), dried over MGS04, filtered and concentrated in vacuo to give a dark yellow oil which was subject to flash chromatography (silica gel) and eluted with 10% EtOAc in hexanes to give a yellow solid (1.6 g, 68%). GCMS 7N/Z 364.0 (M+). H NMR (CDC13/400 MHz) 7.59 (s, 1H), 7.27 (s, 1H), 7.16 (s, 1H), 5.70 (q, 1H, J=7. 0 Hz), 4.29 (m, 2H), 2.19 (s, 3H), 1.32 (m, 3H).

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 2033-24-1, name is 2,2-Dimethyl-1,3-dioxane-4,6-dione, 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. 2033-24-1

The Meldrum’s acid [1] (50.0 g, 347 mmol) and trimethyl orthoformate [2] (184 g) were charged into a 500 mL four-necked flask and heated under reflux for 1 hour. After completion of the reaction, the solvent was removed by an evaporator, and the crude product was recrystallized in a hexane / tetrahydrofuran mixed solvent to give 43.7 g of the compound [66] (yield: 68%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2033-24-1.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; MINAMI, SATOSHI; (157 pag.)TWI588139; (2017); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 105-76-0, name is Dibutyl maleate, molecular formula is C12H20O4, 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. 105-76-0

Example 2 Preparation of 3,6-dimethyl-2(3H)-benzofuranone by Means of Dehydrogenation Using Dibutyl Maleate as Hydrogen Acceptor A mixture of 1000 g of 5,6-dihydro-3,6-dimethyl-2(4H)-benzofuranone, 2000 ml of dibutyl maleate and 50 g of palladium-on-charcoal, 5% by weight, was heated for approx. 3 hours at 170 C. in an autoclave under autogenous pressure. After filtration, the product was purified by fractionating on an 80 cm packed column. Approx. 735 g of pure 3,6-dimethyl-2(3H)-benzofuranone were obtained at a b.p. of approx. 90 C. at 1 mbar.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 105-76-0, its application will become more common.

Reference:
Patent; Haarman & Reimer GmbH; US6391365; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

252881-74-6, A common compound: 252881-74-6, name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Compound C (11.5 mg, 20.2 mumol) and HATU (15.4 mg, 54.7 mumol) were dissolved in DMF (2 mL). DIPEA (35.2 muL, 202 mumol) and tert-butyl 12 amino-4,7,10-trioxadodecanoate (theoretical value 80%) (14.0 mg, ?40.3 mumol) were added to the obtained solution, and the obtained mixture was stirred in an argon atmosphere overnight at room temperature. The solvent was removed in a vacuum, and the residue was refined via HPLC (ODS-C18, A (water and 0.1% TFA):B (CH3CN and 0.1% TFA)=99:1 to 1:99; 20 minutes) to obtain a tert-butyl ester constituting Compound D in the form of a red amorphous solid (LRMS (ESI+): calculated [M+H]+ value: 827; measured value: 827).

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, tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNIVERSITY OF TOKYO; Urano, Yasuteru; Nagano, Tetsuo; Asanuma, Daisuke; Hirose, Kenzo; Namiki, Shigeyuki; Takaoka, Yousuke; (28 pag.)US9784732; (2017); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

6962-92-1, These common heterocyclic compound, 6962-92-1, name is 4-Chlorobutyl 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.

Examples 2 to 13 The process of Example 1 was repeated in a similar manner except that 0.4 mmol of each of the boron compounds as shown in Table 1 was used in place of p-methoxyphenylboronic acid and 0.30 mmol of each organic halide as shown in Table 1 was used in place of 1-bromooctane and reaction was conducted for the noted period of time in Table 1.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6962-92-1.

Reference:
Patent; Sumitomo Chemical Co.,Ltd.; EP1439157; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

623-70-1, 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. 623-70-1, name is Ethyl (E)-but-2-enoate, A new synthetic method of this compound is introduced below.

To a round bottom flask containing ethyl (2E)-but-2-enoate (10.9 g, 87.6 mmol) and CCl 4 (100 mL) were added NBS (17 g, 96 mmol) and AIBN (4.3 g, 26 mmol). The reaction mixture was stirred at 80 for 12 h. The reaction mixture was diluted with DCM and extracted with saturated NaHCO 3, water, and brine. The organic layer was dried over anhydrous Na 2SO 4 and evaporated to dryness to yield the title compound (7.5 g, 44% yield) as an oil.

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; JANSSEN PHARMACEUTICA NV; CAI, Min; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin D.; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (999 pag.)WO2018/103058; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

63106-93-4, name is 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one, 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. 63106-93-4

Diethylamine (1 .56 g, 21 .3 mmol) is added dropwise to a suspension of aluminum trichloride (1 .38 g, 10.4 mmol) in toluene (9.6 mL), cooled to 0 C under magnetic stirring and in nitrogen atmosphere, checking that the internal temperature of the system does not exceed 15 C. The obtained solution is maintained at 25 C for about 30 minutes, then a toluene (2 mL) solution of lactone A (1 .50 g, 8.6 mmol) is slowly added. The mixture is maintained under magnetic stirring at 25 C up to complete conversion (about 2 hours), then poured into water (7.2 mL) previously cooled to 5 C, checking that the internal temperature does not exceed 25 C. The obtained phases are separated and the aqueous phase extracted with toluene. The organic phase is filtered on a panel of activated carbon and celite, and concentrated at reduced pressure until a residue of 2.50 g (containing about 2.10 g of the desired product) is obtained, which is used in the next step without any further purification.

Statistics shows that 63106-93-4 is playing an increasingly important role. we look forward to future research findings about 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one.

Reference:
Patent; QUIMICA SINTETICA, S.A.; BARRECA, Giuseppe; ROMANO’, Bruno Gaetano; (16 pag.)WO2016/71303; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics