Tag: M.W=100-200

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 4934-99-0 as follows. category: esters-buliding-blocks

Step 1: methyl 3-(l,3-dioxo-2,3-dihydro-lH-isoindol-2-yI)cyclobutane-l- carboxylate: into a 1000-mL round-bottom flask, was placed a solution of methyl 3- hydroxycyclobutane-l -carboxylate (10 g, 76.88 mmol, 1.00 eq.) in tetrahydrofuran (500 mL), 2,3-dihydro-l H-isoindole-l,3-dione (13.2 g, 89.7 mmol, 1.20 eq.), triphenyl phosphine (23.6 g, 90.0 mmol, 1.20 eq.). This was followed by the addition of DEAD (21 g, 120.6 mmol, 1.50 eq.) dropwise with stirring. The resulting solution was stirred for 3 h at room temperature. The reaction was then quenched by the addition of water. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 1). This resulted in 6 g (30%) of methyl 3-(l ,3-dioxo-2,3- dihydro-l H-isoindol-2-yl)cyclobutane-l -carboxylate as a white solid. NMR (300MHz, CDC ): delta 7.85-7.81 (m, 2H), 7.75-7.70 (m, 2H), 5.09-5.03 (t, J= 8.7 Hz, 1 H), 3.32-3.29 (m, 1 H), 3.18-3.10 (m, 2H), 2.67-2.59 (m, 2H), 1.31 -1.24 (m, 3H). LC-MS: (M+H)+ = 260.

According to the analysis of related databases, 4934-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; BASTOS, Cecilia, M.; MUNOZ, Benito; TAIT, Bradley; (96 pag.)WO2016/105468; (2016); A1;,
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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. 1162676-00-7, name is Methyl 4-amino-3,5-difluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 4-amino-3,5-difluorobenzoate

EXAMPLE 5 2-[(3,5-Difluoro-4-amino)benzyl]imidazoline hydrochloride Starting with methyl-3,5-difluoro-4-amino benzoate and utilizing consecutively the procedures of Examples 1-4, affords the desired compound.

The synthetic route of 1162676-00-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; US4665095; (1987); A;,
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Synthetic Route of 18927-05-4,Some common heterocyclic compound, 18927-05-4, name is Methyl 3-Methoxyphenylacetate, molecular formula is C10H12O3, 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.

Nitrobenzene (0.4 mmol), methylmethoxyphenylacetate (0.2 mmol),Dimethyl sulfoxide (0.5 mL) and sodium tert-butoxide (0.4 mmol) were successively added to the reaction flask and the reaction was carried out at 45 C for 8 hours. The reaction product was separated from the reaction solution by adding water, dilute hydrochloric acid and ethyl acetate, and the product was isolated by silica gel column chromatography. The yield was 43%, yellow solid,

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-Methoxyphenylacetate, its application will become more common.

Reference:
Patent; Changsha University of Science and Technology; Li Jiangsheng; Yang Fan; Yang Qian; Li Zhiwei; Chen Guoqin; (8 pag.)CN107033006; (2017); A;,
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Related Products of 37746-78-4, 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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows.

Preparation No.61: Preparation of (ii)-ethyl 4-(3-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4- oxadiazol-5-yl)-2-methylphenoxy)but-2-enoate; A 50 mL reaction vial equipped with septa cap outfitted with nitrogen inlet needle was charged with 3-(3-(3-chloro-4-isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-2-methylphenol (0.350 g, 1.015 mmol) and potassium carbonate (0.351 g, 2.54 mmol) in acetone (5.08 mL) to give a colorless suspension. (E)-ethyl 4-bromobut-2-enoate (0.275 mL, 2.030 mmol) was added dropwise via syringe. The resulting suspension was allowed to stir at RT for about 2 days. The reaction mixture was diluted with EtOAc and the solution was washed with 1M HC1 solution (1 x 50 mL), saturated NaHCC>3 solution (1 x 50 mL), and saturated NaCl solution (1 x 50 mL). The organic phase was dried over MgSC>4, filtered and concentrated to give 540 mg of a solid. The sample was purified via automated silica gel chromatography (10%-20% EtOAc : Heptane; EA -40g column, 18 x 150 mm test tubes). The fractions containing product were combined and concentrated to afford (E)-ethyl 4-(3-(3-(3-chloro-4- isopropoxyphenyl)-l,2,4-oxadiazol-5-yl)-2-methylphenoxy)but-2-enoate (353 mg, 76%) as a solid. LC/MS (Table 1, Method k) Rt = 1.98 min, m/z 457 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis (E)-Ethyl 4-bromobut-2-enoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 140-39-6 as follows. Safety of p-Tolyl Acetate

Acetic acid(4-methyl) phenolate 50.0gSoluble in 500ml of carbon tetrachloride, add 4.0g BPO,Stirring at 50 C,Add 71.5g NBS ((4-methyl) phenolate (II) acetate and NBS in 3 batches,The molar ratio of BPO was 1:1.2:0.05), and the reaction was kept for 3 hours. Filtering,The filtrate was concentrated under reduced pressure.The orange-red oil was added dropwise to petroleum ether and stirred to disperse, and a solid precipitated. After suction filtration, the filtrate was washed with water.After drying, it was concentrated under reduced pressure to give (4-bromomethylene) phenyl ester (III), 68.3 g.Yield 89.2%,

According to the analysis of related databases, 140-39-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hubei Guangchen Pharmaceutical Co., Ltd.; Hubei University; Wuhan Institute of Technology; Wang Kai; Liu Dan; Zhao Yimei; Jiang Jun; Kuang Weidong; Zhou Ji; Wu Fengshou; Yang Fang; (7 pag.)CN108640834; (2018); A;,
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Application of 4630-82-4, A common heterocyclic compound, 4630-82-4, name is Methyl cyclohexanecarboxylate, molecular formula is C8H14O2, 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.

Step 1 : 1 -Allyl-cyclohexanecarboxylic acid methyl esterTo a solution of diisopropylamine (10 mL, 72 mmol) in tetrahydrofuran (100 mL) pre-cooled to -69C was added a 2.5 M solution of n-butyllithium in hexanes (29 mL, 72 mmol) dropwise. Following addition, the reaction mixture was warmed to 0C for 30 min and then re-cooled to -70C. To this mixture was added a solution of methyl cyclohexane carboxylate (8.9 mL, 60 mmol) in tetrahydrofuran (30 mL) dropwise. After stirring for 30 min, a solution of allyl iodide (7.2 mL, 78 mmol) in HMPA (5 mL) was added dropwise. The cooling bath was removed to allow the mixture to warm to 20C. After 1 .5 h, the reaction mixture was poured into H2O (200 mL). The two layers were separated and the aqueous layer was extracted with Et2O (100 mL). The organic layers were combined and dried over K2CO3, filtered and concentrated to afford 1 1 g of the title compound as an oil.

The synthetic route of 4630-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI; GAO, Zhongli; HALL, Daniel; STEFANY, David; WO2011/143163; (2011); A1;,
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Related Products of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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.

tert-Butyldimethylsilyl chloride (26.3 g, hydroxycyclohexanecarboxylate (25.0 g, 171 59-80-7) and imidazole (24.7 g, 363174 mmol) was added to a solution of ethyl 4-145 mmol, mixture of cis-/trans-isomers, Gas Nommol) in N,N-dimethylformamide (36 ml) and the mixture was stirred over night at room temperature. For work-up, water was added and the mixture was extracted with tert-butyl methyl ether (3x). The combined organic phases were washed with brine, filtrated through a silicone filter and concentrated under reduced pressure to yield ethyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (43.1 g, 104% yield) which was used in the next step without further purification. 1HNMR (400 MHz, DMSO-d6, mixture of isomers): 6 [ppm] = 4.10-3.99 (m, 2H), 3.93-3.86 (m, 0.7H), 3.63-3.51 (m, 0.3H), 2.39-2.28 (m, 0.8H), 2.27-2.14 (m, 0.3H), 1.91-1.21 (m, 8H), 1.20-1.13 (m, 3H), 0.89-0.79 (m, 9H), 0.08-0.00 (m, 6H).

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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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. 79538-28-6, name is Methyl 2,4,6-trifluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H5F3O2

a) 4-Dimethylamino-2.6-difluoro-benzoic acid methyl ester (6a) To a stirred solution of 4,28 g (22.5 mmol) 2.4,6-Trifluoro-benzoic acid methyl ester (Apollo) and 60.0 ml dimethylsulphoxid are added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture is stirred for 5h at 55C in an autoclave and is reduced with high vacuum rotation evaporator at 65C. The residue is diluted with dichloromethane, washed twice with water. The combined water phases are extracted with dichloromethane. The combined dichloromethane phases are washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude is purified by column chromatography and the desired product 6a is obtained in 74 % yield (3.59 g, 16.7 mmol). MS-ESI: 216 (M+ +1,69).

According to the analysis of related databases, 79538-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1897885; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 51122-91-9, 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. 51122-91-9, name is Dimethyl Isopropylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step (b): After the step (a), the reaction system was cooled to 90C, and (1E)-1,3-dichloro-1-propene (192.3 g) in toluene (250 ml) was added. After 2 hours of heating with stirring, the system was cooled to 50C, and water was added to terminate the reaction. The aqueous layer was extracted with diisopropyl ether (IPE), and the extract was combined with the organic layer and washed with water and 5% aqueous NaCl, successively. The solvent was evaporated under reduced pressure to give dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropylmalonate (409.7 g). The product contained 87% (GC purity) of dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropylmalonate and at most 0.5% (measured by GC) of isopropyl bromide, but did not contain the Z-isomer. 1HNMR (400 MHz, CDCl3): 0.98 (d, 6H, J=6.76), 2.31 (m, 1H), 2.62 (dd, 2H, J=1.16, 7.64), 3.73 (s, 6H), 5.89 (dt, 1H, J=7.60, 13.19), 6.01 (dt, 1H, J=1.16, 13.19). 13CNMR (400 MHz, CDCl3): 18.33, 32.41, 35.14, 51.94, 62.06, 119.83, 128.87, 170.66.

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, Dimethyl Isopropylmalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASAHI GLASS COMPANY LTD.; EP1571138; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 1117-71-1, 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. 1117-71-1 name is Methyl 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.

A solution of methyl (E) -4-bromocrotonate (6 g, 33.5 mmol) in THF (60 mL) was cooled to 0 C, an aqueous solution (20 mL) of lithium hydroxide monohydrate (1.83 g, 43.6 mmol) was added dropwise under N2. After 15 min dripping, keep 0 C for 3 h. The cold water (150 mL) and petroleum ether (200 mL) were then added to the system and stirring was continued at 0 C for 10 min. The aqueous phase was separated, adjusted to pH 1 with concentrated hydrochloric acid at 0 C and extracted with dichloromethane (80 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give E-4-bromocrotonic acid III as a yellow solid (4.5 g, yield 82%).

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

Reference:
Patent; Chengdu Zhipulai Bio-pharmaceutical Technology Co., Ltd.; Wang Kangmin; Zhao Gang; Liu Jifeng; Pu Lin; Chen Wei; (37 pag.)CN106946896; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics