Tag: M.W=100-200

Electric Literature of 37746-78-4, 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. 37746-78-4 name is (E)-Ethyl 4-bromobut-2-enoate, 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: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (E)-Ethyl 4-bromobut-2-enoate, and friends who are interested can also refer to it.

Reference:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
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These common heterocyclic compound, 108928-00-3, name is Ethyl 2,4-difluorobenzoate, 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. SDS of cas: 108928-00-3

2,4-Difluorobenzoic acid ethyl ester (5.33g) was cooled to 0C and treated with concentrated sulfuric acid (3. 5mL) and then fuming nitric acid (3. 5mL). The mixture was stirred for 2 hours at 0C and then partitioned between dichloromethane (2x50mL) and water (25mL). The organic phase was back extracted with water (25mL) and then dried over magnesium sulfate and concentrated in vacuo. This provided the desired compound as a white solid (5. 00g) which was used without further purification.

The synthetic route of Ethyl 2,4-difluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); A1;,
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Related Products of 1234616-21-7,Some common heterocyclic compound, 1234616-21-7, name is Methyl imidazo[1,2-b]pyridazine-6-carboxylate, molecular formula is C8H7N3O2, 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.

Synthesis of imidazo[l,2-b]pyridazin-6-ylmethanol:To a stirred solution of imidazo[l,2-b]pyridazine-6-carboxylate (3.5 g, 22.77 mmol) in MeOH:THF (45 mL, 1 :2) was added NaBH4 (1.72 g, 45.26 mmol) portion wise at 0C and stirred for 2h. After full consumption of starting material by TLC, the reaction was diluted with saturated Na2C03 solution and extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was washed with 50%> EtOAc/Hexane to afford crude imidazo[l,2-b]pyridazin-6-ylmethanol (2.5 g). 1H-NMR (DMSO-d6, 400 MHz): delta 8.21 (s, 1H), 8.06 (d, 1H), 7.21 (s, 1H), 7.24 (d, 1H), 5.68 (br s, 1H), 4.59 (s, 2H); LC-MS: 85.80%; 149.6 (M++l) (column; X-Select C-18, (50×3.0 mm, 3.5mu); RT 0.72 min. 5mM NH4OAc in water: ACN; 0.8 ml/min); TLC: 100% EtOAc (Rf: 0.2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl imidazo[1,2-b]pyridazine-6-carboxylate, its application will become more common.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
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Application of 89-91-8,Some common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, molecular formula is C5H10O4, 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 solution of 2-chlorobenzylamine (30.0 g, 212 mmol) in MeOH (200 mL) was added triethylamine (36.7 mL, 265 mmol) and methyl dimethoxyacetate (31.0 g, 233 mmol). The reaction was heated to 80 C for 20 h. After cooling to room temperature, the reaction wasconcentrated in vacuo. EtOAc (300 ml) was added, washed with iN HC1 (300 mL x 2) and sat. aq. NaHCO3 (300 mL x 2). The organic layer was dried over anhydrous Na2SO4, filtered andconcentrated in vacuo to give the title compound (40.0 g, crude) as colorless oil that required no further purification. ?H NMR (400 IVIFIz, CDC13) 7.39 – 7.33 (m, 2H), 7.24 – 7.21 (m, 2H),4.73 (s, 1H), 4.56 (d, J 6.0 Hz, 2H), 3.38 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,2-dimethoxyacetate, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
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Reference of 4224-69-5, 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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2) To an anhydrous THF solution (2 ml) of the above-obtained Compound (8) (A=-CH=CH-CH=CH-, PG=TBS, 24(E)) (48 mg, 76.8 mumol) were added zinc (powder) (8 mg, 0.12 mmol), methyl 2-(bromomethyl)acrylate (13.8 mul, 0.12 mmol) and a saturated ammonium chloride aqueous solution (0.7 ml) at 0C, and the mixture was stirred for 30 min at room temperature. The reaction was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by column chromatography (5%?20% ethyl acetate in hexane) to obtain Compound (C) (60 mg, 107% yield). Compound (C):1H NMR (CDCl3) delta : 0.055 (s, 3 H), 0.059 (s, 3 H), 0.062 (s, 6 H), 0.55 (s, 3 H), 0.88 (s, 18 H), 1.04 (d, J=6.6 Hz, 3 H), 1.23-2.17 (m, 15 H), 2.18-2.24 (m, 1 H), 2.42-2.52 (m, 2 H), 2.60-2.65 (m, 1 H), 2.78-2.86 (m, 1 H), 3.74 (s, 3 H), 4.19-4.22 (m, 1 H), 4.28-4.34 (m, 1 H), 4.34-4.39 (m, 1 H), 4.86 (d, J=2.2 Hz, 1 H), 5.17 (s, 1 H), 5.53-5.62 (m, 1 H), 5.67 (d, J=1.2 Hz, 1 H), 5.90-6.03 (m, 2 H), 6.15-6.25 (m, 2 H), 6.26 (d, J=1.2 Hz, 1 H). MS m/z 747 (M+23)+.

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-(bromomethyl)acrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TEIJIN LIMITED; EP1477483; (2004); A1;,
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Related Products of 924-99-2, A common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

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; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
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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. 103-09-3, name is 2-Ethylhexyl acetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H20O2

In the mechanical stirrer, reflux condenser and a thermometer of the 1000 ml flask of three sequentially added in the methyl acetate 296 g, isooctanol 260 g toluene sulfonic acid and 13.0 g, stir, for 65 C reaction 4 hours. By reducing pressure low boiling, then adding to the methoxy benzaldehyde 180 g, dropping 30% of 36 g liquid sodium methoxide. The reaction temperature is raised to 90 C, reaction 4 hours later. Gradually adding glacial acetic acid 7.9 g out-in and. By reducing pressure low boiling, filtering to remove the mother liquor solids, then the gas phase chromatography analysis, calculated in the mother liquor to the methoxy cinnamic acid ester product 376 g, yield 98.2%.

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; Shandong Daguan Biochemical Technology Co., Ltd.; Qingdao University of Science and Technology; Zhang Yongfu; Liu Baowei; Xu Zhihua; Jiang Yunbing; Yang Fengke; (6 pag.)CN107522616; (2017); A;,
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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, SDS of cas: 22223-49-0

Step B Preparation of methyl 2-[[(2,2-dimethylhydrazino)carbonyl]amino]-3-methylbenzoate To a solution of the title compound of Step A (25.4 g, 154 mmol) in p-dioxane (500 mL) under a nitrogen atmosphere was added diphosgene (22.3 mL, 184 mmol), followed by triethylamine (25.6 mL, 184 mmol). A white precipitate formed, and the resulting mixture was heated to 60 C. overnight. The mixture was cooled to room temperature and filtered. The precipitate was washed with diethyl ether and the combined filtrates were concentrated under reduced pressure to afford an oil (30.97 g) which, without further characterization, was dissolved in toluene (400 mL). To this solution at 0 C. under a nitrogen atmosphere was added 1,1-dimethylhydrazine (12.3 mL, 162 mmol) and the resulting milky suspension was stirred at 0 C. for 30 min. The precipitate was collected by filtration and washed with hexanes to afford the title compound of Step B (25.57 g) as a beige solid. 1 H NMR (CDCl3): delta 9.22 (br s,1H), 7.75 (d,1H), 7.40 (d,1H), 7.14 (t,1H), 5.32 (br s,1H), 3.88 (s,3H), 2.66 (s,6H), 2.35 (s,3H).

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; E. I. du Pont de Nemours and Company; US5962436; (1999); A;,
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Adding a certain compound to certain chemical reactions, such as: 4897-84-1, name is Methyl 4-bromobutanoate, 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 4897-84-1, SDS of cas: 4897-84-1

To a solution of 3-bromophenol (3.44 g, 20.0 mmol) and methyl 4-bromobutanoate (4.32 g, 24.0 mmol) in DMF (20 mL) was added K2co3 (5.52 g, 40.0 mmol). The mixture was stirred at rt for 0.5 h and then heated with stirring at 90 oC for 1 h. After diluting with EtOAc (200 mL), the mixture was washed with water (3 x 50 mL), dried and concentrated. The crude product was purified by silica gel column chromatograph (petroleum/EtOAc = 10:1) to give methyl 4-(3- bromophenoxy)butanoate as a white liquid (5.2 g, yield: 96percent). ESI-MS (M+H) +: 273.1

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; BIOGEN MA INC.; HOPKINS, Brian, T.; MA, Bin; PRINCE, Robin; MARX, Isaac; LYSSIKATOS, Joseph, P.; ZHENG, Fengmei; PETERSON, Matthew; PATIENCE, Daniel, B.; (205 pag.)WO2018/191577; (2018); A1;,
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10601-80-6, name is Ethyl 3,3-diethoxypropionate, 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 3,3-diethoxypropionate

4-Chloro-2-nitrobenzaldehyde (3.71 g, 0.02 mol) was dissolved in ethanol (40 ml).Further adding stannous chloride (18.04g, 0.08mol) and ethyl 3,3-diethoxypropionate (9.5g, 0.05mol), and reacting at 90 C for 4 hours, the reaction of the raw materials of the plate is completed; After the solvent was added, ethyl acetate was dissolved, and neutralized to a weak basic with saturated sodium carbonate; filtered, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate, and then the organic layer was combined, and then evaporated to dryness. Ethyl acetate = 10:1, then petroleum ether: ethyl acetate = 5:1) After washing, ethyl 7-chloro-3-quinolinecarboxylate (3.478 g, 74%).

The synthetic route of 10601-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Kangrun Pharmaceutical Co., Ltd.; Jin Haowen; Xu Weiliang; Xu Weizheng; (8 pag.)CN108484497; (2018); A;,
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