Month: July 2021

These common heterocyclic compound, 18830-44-9, name is Methyl 3,3,3-trifluoropropanoate, 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. Recommanded Product: 18830-44-9

General procedure: R2BCl (2.0 mmol) was added dropwise to the solution of ester (1.0 mmol) and amine (3.0 mmol) in dichloromethane (3.5 mL) at -78 C and stirred at the same temperature for 1.5 h. Aldehyde (1.5 mmol) dissolved in dichloromethane was then added dropwise to the above reaction mixture and stirred at -78 C for 1 h and 0 C for 1 h. The reaction was quenched by the addition of pH 7 buffer solution (2 mL). The mixture was diluted with MeOH (2 mL), followed by the careful addition of 30% hydrogen peroxide (2 mL) and stirred vigorously for 4-5 h. The reaction mixture was partitioned between water (4 mL) and dichloromethane. The aqueous layer was extracted with dichloromethane (3 x 10 mL) and the combined organics were washed with brine (5 mL), dried (anhydrous Na2SO4), filtered, concentrated and purified by silica gel chromatography to obtain the pure aldol product.

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

Reference:
Article; Veeraraghavan Ramachandran; Gagare, Pravin D.; Parthasarathy, Gowrisankar; Tetrahedron Letters; vol. 52; 46; (2011); p. 6055 – 6057;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 34846-90-7, name is Methyl 3-methoxyacrylate, 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 34846-90-7, Recommanded Product: 34846-90-7

Example 2 The toluene solution of 3-mercapto-2-butanone from the previous step (613 g of ca. 25 wtpercent solution) was placed in a clean, dry reactor along with 15 g of methyl-3-methoxyacrylate. The mixture was warmed to 25°C, stirred vigorously, and treated with solid sodium methoxide (8.5 g, ca. 0.1 equiv.) all at once. The remaining methyl-3-methoxyacrylate (151 g) was added in at a rate to keep the temperature at or below 35°C (2 h). The resulting mixture was allowed to reach room temperature and stir for 21 h. Concentrated hydrochloric acid (88 g) was added to the mixture over 30 min such that the temperature did not exceed 35°C. The resulting mixture was stirred vigorously for 2 h, then treated with 73 g of water, and stirred for 10 min more. The phases were allowed to separate. After standing for 10 min, the aqueous phase was drained from the reactor, and the upper, product phase was washed with 100 g of 5percent sodium bicarbonate solution. After being stirred for 15 min, the phases were allowed to separate. The lower, aqueous phase was drained from the reactor, and the upper. product phase was transferred to a distilling flask. The toluene was distilled through a 5-plate distillation column at 13.3 kPa [100 mmHg]. After a small fraction containing toluene and other low boiling impurities was collected, the product, 3-carbomethoxy-4,5-dimethylthiophene, was distilled through the column at 6.665 kPa [150 mmHg].

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 3-methoxyacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Monsanto Technology LLC; EP1023283; (2003); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 34846-90-7 as follows. Formula: C5H8O3

A mixture of methyl-3-methoxypropenoate, 37-f, (13.92 g, 120 mmol), N- iodosuccinimid (32g, 140mmol), glacial acetic acid (18 mL, 240 mmol), and dichloromethane(150 mL) was stirred at room temperature for 24h. Triethylamine (50 mL, 36 mmol) was added, and the reaction mixture was stirred at room temperature for 12h before water was added. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, and water, and were dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash chromatography (PE:EA=1 :5) to afford compound, 37-g (30.5 g, crude) . 1H NMR (300 MHz, CDCI3) delta 7.69 (s, 1H), 4.01 (s, 3H), 3.80 (s, 3H); LC-MS (ESI): 243 [M+H]+

According to the analysis of related databases, 34846-90-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Changyou; ZOU, Wuxin; HUA, Yuxia; DANG, Qun; WO2013/40790; (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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Ethyl 3,3-diethoxypropionate

General procedure: A mixture of Yb(OTf)3 (2.5 mol%), amine (1.0 eq.), ethyl 3,3-diethoxypropionate (2.5 eq.) and aldehyde (1.1 eq.) in 1,4-dioxane (1.5 mL / 1 eq.) was stirred at 90 C for 6-17 h. After the reaction, the resulting mixture was washed with PBS buffer solution (25 mL) and extracted with CH2Cl2 (15 mL×3). The organic layer was dried over MgSO4. Removal of the solvent in vacuo, followed by chromatography on silica gel column (AcOEt/Hexane or CHCl3/MeOH), afforded dihydropyridine 4.

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

Reference:
Article; Sueki, Shunsuke; Takei, Ryo; Abe, Junya; Shimizu, Isao; Tetrahedron Letters; vol. 52; 34; (2011); p. 4473 – 4477;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 23786-14-3,Some common heterocyclic compound, 23786-14-3, name is Methyl 4-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.

Preparation 6a: Methyl bromo(4 tate; To a mixture of methyl 4-methoxyphenylacetate (20 g, 0.11 mol) and NBS (0.11 mol) in CCI4 (0.2 I) were added 3 drops of 48% HBr and this mixture was heated to reflux for 8 h. The cooled solution was filtered through a pad of silica gel and the filtrate was evaporated in vacuo to give 29 g of the title compound as pale yellow oil, which was used in the subsequent step without further purification.NMR (1H, CDCI3): delta 7.3 (d, 2H), 6.8 (d, 2H), 5.1 (s, 1 H), 3.8 (s, 3H), 3.5 (s, 3H).

The synthetic route of 23786-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/108700; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 756525-95-8,Some common heterocyclic compound, 756525-95-8, name is tert-Butyl 9-Amino-4,7-dioxanonanoate, molecular formula is C11H23NO4, 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.

Compound 422 (0.50 g, 1.0 mmol) and DIPEA (0.4 mL, 2.4 mmol) were dissolved in DCM (5.0 mL) at 0 , and then compound 301 (0.23 g, 1.0 mmol) was added. The reaction was stirred at 0 for 2.5h, then concentrated and purified by SiO2column to give the title product 423 (0.30 g, 43%) . ESI m/z calcd for C31H45N5O11P [M+H]+: 694.28, found 694.28.

The synthetic route of 756525-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 148547-19-7, 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 148547-19-7 as follows.

To a solution of methyl 4-bromo-3-methylbenzoate (ABCR, 15 g, 65 mmol) in toluene (200 ml.) and water (200 ml_), was added o-tolylboronic acid (10.68 g, 78 mmol) followed by potassium carbonate (45.25 g, 32.7 mmol) and Pd(PPh3)4 (3.78 g, 3.3 mmol). The mixture was degassed with N2 and refluxed at 1200C for 6 hours. After the completion of reaction, the reaction mixture was cooled to RT. The organic phase was separated and evaporated under reduced pressure. The crude compound was passed through a silica column (60-120) using hexane as eluent to get the title compound as a white solid (15 g, 95%). 1H NMR (DMSO-dbeta, 400 MHz) delta 7.91 (s, 1 H), 7.83-7.81 (m, 1 H), 7.33-7.30 (m, 2H), 7.28-7.26 (m, 1 H), 7.25-7.22 (m, 1 H), 7.07-7.05 (d, 1 H), 3.86-3.81 (s, 3H), 2.09-2 (s, 3H), 1.97-1.92 (s, 3H).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; GERBER, Patrick; DORBAIS, Jerome; WO2010/100142; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 24812-89-3, These common heterocyclic compound, 24812-89-3, name is Methyl 3-amino-2,4-dimethylbenzoate, 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.

Scheme 23. step A. To a solution of 2-chloroquinoline-4-carboxylic acid (0.40 g,0.0019 mol) in CH2Ch (8 mL) at 0C are added methyl3-amino-2,4-dimethylbenzoate(0.31 g, 0. 0017 mol, see preparation 10) and triethylamine (0.80 ml, 0.0058 mol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride(50% solution in ethyl acetate, 2.45 ml, 0.0038 mol) is added via syringe and stirred at room temperature. After 16 hours, the reaction is diluted with water and extracted twicewith dichloromethane. The organic layers are combined and dried over magnesiumsulfate, filtered, and concentrated under reduced pressure. The resulting residue istriturated with 20% diethyl ether in pentane and filtered to give the title compound as an off-white solid (0.55 g, 77 %). Mass spectrum (m/z): 369.1 (M+1).

Statistics shows that Methyl 3-amino-2,4-dimethylbenzoate is playing an increasingly important role. we look forward to future research findings about 24812-89-3.

Reference:
Patent; ELI LILLY AND COMPANY; BLANCO-PILLADO, Maria-Jesus; VETMAN, Tatiana Natali; FISHER, Matthew Joseph; KUKLISH, Steven Lee; WO2014/4230; (2014); 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. 927-68-4, name is 2-Bromoethyl acetate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 927-68-4

In a 40 mL reaction vial under nitrogen gas, was added (1977) 2-amino-5-bromopyridin-3-ol (0.320 g, 1.693 mmol) and DMF (5 mL). The mixture was cooled to 5 C and NaH (0.102 g, 2.54 mmol) was added. The reaction mixture was stirred at 5 C for 1 hour. Next, 2-bromoethyl acetate (0.283 mL, 2.54 mmol) was introduced neat via a syringe. The reaction mixture was stirred at 5 C and slowly warmed to room temperature overnight. The mixture was cooled to 5 C and carefully diluted with water. Ethyl acetate was added and the mixture was transferred to a separatory funnel. The layers were separated and the organics were washed with brine, dried over sodium sulfate, filtered and concentrated to afford (1978) 2-((2-amino-5-bromopyridin-3-yl)oxy)ethyl acetate as a tan oil (0.45 g, 97%). LC-MS: M+1= 275/277, rt = 0.52 min, [Al].

According to the analysis of related databases, 927-68-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; HAQUE, Tasir Shamsul; LOMBARDO, Louis J.; MACOR, John E.; MUSSARI, Christopher P.; PASUNOORI, Laxman; RATNA KUMAR, Sreekantha; SHERWOOD, Trevor C.; POSY, Shoshana L.; SISTLA, Ramesh Kumar; HEGDE, Subramaya; RAMACHANDRA, Anupama; (425 pag.)WO2018/5586; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, 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 24393-53-1, category: esters-buliding-blocks

Example 1; 4′-((1S.2SV2-ir(2S)-2-MethylPyrrolidin-1-v?methyllcvcloproDvn-1.1′-biphenyl-4- carbonitrile; Example 1A; fra/7S-3-(4-Bromophenyl) prop-2-en-1 -ol; To a solution of ethyl trans-4-bromocinnamate (8 ml_, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at -780C dropwise. After the addition, the mixture was allowed to warm from -78 0C to -30 0C over two hours. The mixture was then cooled back to -780C and aqueous 1 N HCI was added till acidic (pH=2). The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried withMgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.44 (t, J = 6 Hz1 1H)1 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt, J = 16.5 Hz, J = 6 Hz1 1H), 6.57 (dt, J =15 Hz, J =3 Hz, 1H), 7.25 (d, J = 9 Hz, 2H), 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H)+.; Example 26; 4′-(f1R.2S)-2-(2-ff2R)-2-Methylpyrrolidin-1-yl1ethyl>cvclopropyh-1.1′-biphenyl-4- carbonitrile; Example 26A; 3-(4-BromophenvQprop-2-ene i-p|; To a solution of ethyl trans-4-bromocinnamate [CAS 24393-53-1] (8 mL, 42.6 mmol) in anhydrous dichloromethane (150 mL) under N2 was added dropwise diisobutylaluminum hydride in dichloromethane (128 mL, 1M, 128 mmol) at -780C. Following the addition, the mixture was allowed to warm from -780C to -300C over two hours. The mixture was then cooled back to -780C and aqueous 1 N HCI was added. The organic layer was separated, dried with MgSO4, filtered and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.44 (t, J = 6 Hz, 1 H), 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt. J = 16.5 Hz, J = 6 Hz1 1H), 6.57 (dt, J =15 Hz1 J =3 Hz, 1H), 7.25 (d. J = 9 Hz, 2H), 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H); Example 34; 2-r4-((1S.2S)-2-(f(2S)-2-MethylPyrrolidin-1-yllmethyl)cvclopropyhphenyllPyridazin- 3(2H)-one; Example 34A; (E)-3-(4-bromophenyl)prop-2-en-1-ol; To a solution of (E)-ethyl 3-(4-bromophenyl)acrylate (25 g, 96 mmol) inDCM (300 ml) under nitrogen and cooled to -78 0C was added dropwise DIBAL-H (240 ml, 1 M in DCM, 240 mmol) in about 20 minutes. The mixture was stirred at -780C for 2 hours. Then, the dry ice bath was removed. The reaction was diluted with DCM (500 ml_), quenched with HCI (1N), and partitioned. The combined organic phases were washed with HzO, dried and concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, CDCI3): delta 1.43 (t, J = 6 Hz1 1H), 4.32 (t, J = 4.5 Hz, 2H), 6.37 (dt, J = 16.5 Hz, J = 6 Hz, 1H), 6.57 (d, J =15 Hz, 1H), 7.25 (d, J = 9 Hz, 2H)1 7.45 (d, J = 9 Hz, 2H). MS (DCI-NH3) m/z 214 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; WO2007/150010; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics