Category: 110104-60-4

Synthetic Route of 110104-60-4,Some common heterocyclic compound, 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, molecular formula is C6H9ClO3, 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 4-phenoxyaniline (10 g) and acetonitrile (40 mL) was added a mixture of methyl 4-chloro-3-methoxy-2-(E)-butenoate (9.18 mL) and acetonitrile (40 mL) at 0 C. To the reaction mixture was added a mixture of triethylamine (8.28 mL) and acetonitrile (20 mL) at 0 C. The reaction mixture was heated under reflux for 4 hr and cooled to room temperature. The precipitate was removed by filtration. To the filtrate was added water (80 mL), and the mixture was adjusted to pH 3 with concentrated hydrochloric acid. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. To the residue were added toluene (80 mL) and acetic acid (2.0 mL) at room temperature. The reaction mixture was heated at 50 C. for 1.5 hr. The reaction mixture was diluted at room temperature with water, saturated brine and saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (7.43 g). MS: [M+H]+ 281.8.

The synthetic route of 110104-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOIKE, Tatsuki; FUSHIMI, Makoto; AIDA, Jumpei; IKEDA, Shuhei; KUSUMOTO, Tomokazu; SUGIYAMA, Hideyuki; TOKUHARA, Hidekazu; (170 pag.)US2016/318864; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, 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. HPLC of Formula: C6H9ClO3

A) 1-(3-Iodophenyl)-4-methoxy-1H-pyrrole-2(5H)-one To a mixture of 3-iodoaniline (5.32 g) and tetrabutylammonium iodide (0.897 g) in acetonitrile (20 mL) was added a mixture of methyl 4-chloro-3-methoxy-2-(E)-butenoate (4.13 mL) and acetonitrile (20 mL). To the reaction mixture was added a mixture of triethylamine (3.72 mL) and acetonitrile (10 mL). The reaction mixture was stirred overnight at 50 C. To the reaction mixture were added methyl 4-chloro-3-methoxy-2-(E)-butenoate (1.65 mL) and triethylamine (1.69 mL). The reaction mixture was stirred at 50 C. for 5 hr and cooled to room temperature. The reaction mixture was adjusted to pH 3 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. To the residue were added toluene (40 mL) and acetic acid (1.0 mL) at room temperature. The reaction mixture was heated at 50 C. for 1.5 hr. The reaction mixture was concentrated under reduced pressure and crystallized from methanol/diisopropylether to give the title compound (3.41 g). MS: [M+H]+ 316.0.

The synthetic route of (E)-Methyl 4-chloro-3-methoxybut-2-enoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOIKE, Tatsuki; FUSHIMI, Makoto; AIDA, Jumpei; IKEDA, Shuhei; KUSUMOTO, Tomokazu; SUGIYAMA, Hideyuki; TOKUHARA, Hidekazu; (170 pag.)US2016/318864; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, 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. Safety of (E)-Methyl 4-chloro-3-methoxybut-2-enoate

A suspension of (S)-2-amino-3-cyclopentyl-propionic acid methyl ester hydrochloride (1.92 g, 9.13 mmol) in acetonitrile (18 mL) was treated with triethylamine (1.3 mL, 9.34 mmol). The mixture was then heated to 60 C., and kept at that temperature for 1 h. Then, additional triethylamine (1.3 mL, 9.34 mmol) was added followed by methyl-4-chloro-3-methoxy-(E)-2-butenoate (1367 mg, 8.30 mmol) in acetonitrile, via a syringe drop wise. The mixture was then heated to reflux by lowering into a pre-heated oil bath kept at 100 C. for 18 h, under nitrogen. The mixture was cooled to 25 C., and the precipitated triethylammonium hydrochloride was filtered off. The supernatant was concentrated and purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 120 g; 0% to 100% ethyl acetate/hexanes) to afford, (S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester (1.42 g, 58.2%) as light yellow oil: 1H NMR (DMSO-d6, 300 MHz) delta ppm 1.06 (m, 2 H), 1.36-1.90 (m, 9H), 3.61 (s, 3H), 3.77 (s, 3H), 3.94 (AB, Jgem=17.8 Hz, 2H), 4.62 (dd, J=4.8 Hz, 11.0 Hz, 1 H), 5.16 (s 1H).

The synthetic route of 110104-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berthel, Steven Joseph; Brinkman, John A.; Hayden, Stuart; Haynes, Nancy-Ellen; Kester, Robert Francis; McDermott, Lee Apostle; Qian, Yimin; Sarabu, Ramakanth; Scott, Nathan Robert; Tilley, Jefferson Wright; US2009/264445; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H9ClO3

Example-113 Potassium carbonate (95 mg, 0.69 mmol) and methyl (E)-4-chloro-3-methoxy-2-butenoate (114 mg, 0.69 mmol) were added to a solution of 5-chloro-4-(4-chloro-2-fluoro-5-hydroxyphenyl)-1,2-tetramethylene-4-pyrazolin-3-one (200 mg, 0.63 mmol) in DMF (2 mL), followed by stirring at 50 C. for 5 hours. After the reaction was completed, water (20 mL) was added to the reaction solution, and the resultant product was extracted with ethyl acetate (20 mL*2, 10 mL*1). The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and was concentrated under reduced pressure, whereby a pale yellow oily crude product (319 mg) was obtained. This was purified by silica gel column chromatography (ethyl acetate), whereby methyl (E)-4-[2-chloro-5-(5-chloro-3-oxo-1,2-tetramethylene-4-pyrazolin-4-yl)-4-fluorophenyloxy]-3-methoxy-2-butenoate (283 mg, yield: quantitative) was obtained as a pale yellow oily material. 1H-NMR (400 MHz, CDCl3): delta1.87-1.92 (m, 2H), 1.99-2.03 (m, 2H), 3.60-3.62 (m, 2H), 3.69 (s, 3H), 3.72 (s, 3H), 3.80-3.83 (m, 2H), 5.21 (s, 1H), 5.27 (s, 2H), 7.13 (d, J=6.3 Hz, 1H), 7.17 (d, J=9.1 Hz, 1H). 19F-NMR (376 MHz, CDCl3): delta-119 (s, 1F).

According to the analysis of related databases, 110104-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, 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 110104-60-4, Quality Control of (E)-Methyl 4-chloro-3-methoxybut-2-enoate

Genera procedure: To a solution of the corresponding alkyl amine (1.2 equiv) in THF (2.0 M) was added simultaneously a solution of (E)-4-chloro-3-methoxy-but-2-enoic acid methyl ester (1 equiv) in acetonitrile (1.5 M) and a solution of triethylamine (1 equiv) in acetonitrile (3.6 M) over 30 min at room temperature. After stirring overnight at room temperature or 3 h at 55 C, the resulting precipitate in the reaction mixture was removed by filtration. The mother liquor was concentrated and purified by flash chromatography on silica gel eluting with a gradient of 20-100% ethyl acetate in hexanes to afford the title compound in greater than 75% yield.

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, (E)-Methyl 4-chloro-3-methoxybut-2-enoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 110104-60-4, These common heterocyclic compound, 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, 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.

EXAMPLE 2 Production of 4-methoxy-2(5H) thiophenone from 4-chloro-3-methoxy-2E-butenoic acid methyl ester and sodium hydrogen sulfide 11.6 g (0.14 mol) of 90 percent sodium hydrogen sulfide monohydrate is dissolved in 90 ml of methanol. A solution of 17.0 g (0.1 mol) of 96.7 percent 4-chloro-3-methoxy-2E-butenoic acid methyl ester in 10 ml of methanol is instilled into this solution at 50 C. in 4 hours. It is stirred for another 2 hours and the methanol is then distilled off under vacuum on the rotary evaporator. The residue is mixed with 100 ml of water and extracted twice with 80 ml each of methylene chloride. The organic phase is dried over sodium sulfate and concentrated by evaporation. The residue is recrystallized hot from 15 ml of ethanol. 5.12 g of yellow-colored product with a melting point of 90 C. is obtained. Further data concerning the compound is: content (GC): 96 percent; yield: 37.8 percent.

Statistics shows that (E)-Methyl 4-chloro-3-methoxybut-2-enoate is playing an increasingly important role. we look forward to future research findings about 110104-60-4.

Reference:
Patent; Lonza Ltd.; US4906759; (1990); 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. 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, A new synthetic method of this compound is introduced below., Safety of (E)-Methyl 4-chloro-3-methoxybut-2-enoate

Genera procedure: To a solution of the corresponding alkyl amine (1.2 equiv) in THF (2.0 M) was added simultaneously a solution of (E)-4-chloro-3-methoxy-but-2-enoic acid methyl ester (1 equiv) in acetonitrile (1.5 M) and a solution of triethylamine (1 equiv) in acetonitrile (3.6 M) over 30 min at room temperature. After stirring overnight at room temperature or 3 h at 55 C, the resulting precipitate in the reaction mixture was removed by filtration. The mother liquor was concentrated and purified by flash chromatography on silica gel eluting with a gradient of 20-100% ethyl acetate in hexanes to afford the title compound in greater than 75% 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:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, 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 110104-60-4, COA of Formula: C6H9ClO3

General procedure: Example-115 In the same manner as in Example-12 except that cesium carbonate was used instead of potassium carbonate, from 5-chloro-4-(2,4-dichloro-5-hydroxyphenyl)-1,2-tetramethylene-4-pyrazolin-3-one and methyl (E)-4-chloro-3-methoxy-2-butenoate, methyl (E)-4-[5-(5-chloro-3-oxo-1,2-tetramethylene-4-pyrazolin-4-yl)-2,4-dichlorophenyloxy]-3-methoxy-2-butenoate was obtained with a yield of 86%. 1H-NMR (400 MHz, CDCl3): delta1.87-1.94 (m, 8H), 1.99-2.06 (m, 2H), 3.58-3.63 (m, 2H), 3.69 (s, 3H), 3.70 (s, 3H), 3.80-3.85 (m, 2H), 5.20 (s, 1H), 5.28 (s, 2H), 6.97 (s, 1H), 7.46 (s, 1H).

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; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics