Month: July 2021

These common heterocyclic compound, 14064-10-9, name is Diethyl 2-chloromalonate, 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: 14064-10-9

General procedure: A mixture of diethyl chloromalonate (19.1 mmol) and suitable sodium phenate (20.1 mmol), prepared from an equivalent amount of the corresponding phenol and sodium in abs EtOH, was stirred and heated under reflux in acetone (100 mL) for 4 h. The solvent was removed under reduced pressure, the residue was taken up with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated to give an oily residue which was chromatographed on silica gel column (petroleum ether/ethyl acetate 9:1 as eluent). The desired compounds were obtained as pale yellow oils in 14-77percent yield.

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

Reference:
Article; Fracchiolla, Giuseppe; Laghezza, Antonio; Piemontese, Luca; Parente, Mariagiovanna; Lavecchia, Antonio; Pochetti, Giorgio; Montanari, Roberta; Giovanni, Carmen Di; Carbonara, Giuseppe; Tortorella, Paolo; Novellino, Ettore; Loiodice, Fulvio; Bioorganic and Medicinal Chemistry; vol. 20; 6; (2012); p. 2141 – 2151;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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. category: esters-buliding-blocks

In one example of the inventive process, the reaction was conducted with methyl 3-amino-4-chloro-benzoate and 1-cyclopentyl-2-pyridinyl acetylene as the starting materials (Scheme 7). Suitable choices of ligand, base and solvent was important for obtaining satisfactory results as shown in Table 1. Several ligands were examined. It was found that the reaction proceeded smoothly to afford the desired indole product when using either ligand 4a, 4b or 5 in the presence of n-Bu4N+OAc-. The major side-reaction was homocoupling of the arylchloride via double amination (entries 1-3). The proper choice of base, solvent, temperature, and concentration was important to minimize the formation of the amination byproduct and also maximize the desired regioselectivity. By using inorganic bases such as K2CO3, a cleaner reaction could be obtained than by using n-Bu4N+OAc- as base. When a ferrocene ligand such as bis(diisopropylphosphino)ferrocene was employed, in combination with K2CO3 as base, the indolization of 2-chloroaniline with the internal acetylene completed rapidly, providing the product in high purity and regioselectivity (entry 4). Addition of LiCl or LiI as additive did not improve the yield. Instead, it slowed down the reaction (entries 5-6). With reduced catalyst loading (5 mol %), the reaction also proceeded smoothly and cleanly (entry 7). Changing the ratio of ligand to palladium acetate from 2:1 to 1:1 prolonged the reaction time (entry 8). Using K2CO3 as base, ligands 4a, 4b or 6 also afforded good results (entries 9-10). The wavelength used was 240 nm. TABLE I Base Time Entry (Scale) (eq) Catalyst (h) Result* 1 (100 mg) n-Pd(OAc)2 (10%) 4 Complete conversion of Bu4N+OAc- 2-(Di-t- starting material, giving 45 (2.5 eq) butylphosphino)- area % product and 33 biphenyl (40%) area % byproduct. 2 (100 mg) n-Pd(OAc)2 (10%) 3 Ratio of the desired product Bu4N+OAc- 1,1′- to starting material (2.5 eq) Bis(diphenylphosphino) (cholroaniline) was 5:1, ferrocene(20%) about 35 area % unknown impurities. The ratio of the regioisomers was 9:1. 3 (200 mg) n-Pd(OAc)2 (10%) 14 Complete conversion of the Bu4N+OAc- 1,1′-Bis(di-i- starting material, about 35 (2.5 eq) propylphosphino) area % of unknown ferrocene(20%) impurities. The ratio of the regioisomers was 9:1. 28% isolated yield was obtained through column chromatography for two steps. 4 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 3 Complete conversion of the 1,1′-Bis(di-i- starting material. The propylphosphino) desired product was formed ferrocene(20%) in 88 area % purity. The ratio of the regioisomers was 20:1. 5 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 Ratio of the desired product 1,1′-Bis(di-i- to the starting material was LiCl (1 eq) propylphosphino) 14:1. The ratio of the ferrocene(20%) regioisomers was 19:1. 6 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 The ratio of the desired 1,1′-Bis(di-i- product to the starting LiI (1 eq) propylphosphino) material was 1.6:1. ferrocene(20%) 7 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 5:1. The ratio ferrocene(10%) of regioisomers was 18:1. 8 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 2.5:1. The ferrocene(6%) ratio of regioisomers was 19:1. 9 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 Complete conversion of the 2-(Di-t- starting material, with about butylphosphino)- 20 area % impurities. The biphenyl (10%) ratio of the regioisomers was 20:1. 10 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired Tricyclohexylphosphine product to the starting (10%) material was 4:1. Ratio of the regioisomers was 18:1. *Ratios of product were measured by HPLC analysis

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40872-87-5, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 140-11-4, These common heterocyclic compound, 140-11-4, name is Benzyl 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.

In a 5 ml glass bottle into which the magnet was placed,Then add NaOEt (17 mg, 0.25 mmol),The catalyst E (0.38 mg, OOl mmol),Benzyl acetate (0. 7508 g, 5 mmol, S / C = 10000: 1),Solvent dioxane (2.5 mL),The above reaction system was placed in a high-pressure reactor, Replacement of hydrogen three times,Charged with hydrogen gas of 50 atm,The reaction vessel was placed in a 80 C oil bath,Heating and stirring 16h,The reaction vessel was cooled in an ice bath.The reaction system was analyzed by gas chromatography (SPBTM-5, FUSEDSILICA Capillary Column, 30mX0.25mmX0.25ym, filmthickness)Injection temperature of 250 C,Detection temperature 260 C, program temperature 120 C (0 C) -20 C / min to 240 C (Omin). Gas chromatographic analysis yielded 82%.

The synthetic route of 140-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WUHAN KAITE LISI TECHNOLOGY CO LTD; Zhang, Xumu; Tan, xuefeng; (15 pag.)CN104387418; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference 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.

4-Methoxybenzylamine (29.8 g, 217.2 mmol) was dissolved in ethanol (1 L), N,N-diisopropylethylamine (84.25 g, 651.6 mmol) was added, ethyl 4-bromocrotonate (75%, 122.96 g, 477.84 mmol) was slowly added, heated to 40C by using oil-bath, reacted for 16h. After completion of the reaction as measured by TLC (petroleum ether : ethyl acetate =5:1), the reaction solution was concentrated in vacuum, water (500 mL) was added, extracted with ethyl acetate (500 mL*2), the organic phases were combined and concentrated in vacuum, the crude product was purified by silica gel column chromatography (petroleum ether : ethyl acetate =10:1) to obtain the title compound (76 g, yield 96.8%).

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:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (77 pag.)EP3281942; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 681128-38-1, 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. 681128-38-1, name is Ethyl 3,3-difluorocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

NaOH (10.7 g, 0.268 mol) was dissolved in MeOH (100 mL) and H2O(100 mL). Ester 23 (40.0 g, 0.244 mol) was added at r.t., and the resulting mixture was stirred at r.t. for 15 h, then evaporated in vacuo to half of the volume, acidified with concd aq HCl to pH 1, and extracted with CH2Cl2 (3 × 350 mL). The combined organic extracts were evaporated in vacuo.Yield: 32.4 g (98%); white solid; mp 49-52 C. 1H NMR (500 MHz, CDCl3): delta = 12.11 (br s, 1 H), 3.06-2.96 (m, 1 H), 2.94-2.79 (m, 4 H). 13C NMR (125 MHz, CDCl3): delta = 179.6, 118.0 (dd, J = 284, 271 Hz), 38.1(t, J = 24.8 Hz), 26.0 (dd, J = 14.0, 5.7 Hz). 19F NMR (376 MHz, CDCl3): delta = -84.5 (d, J = 194 Hz), -97.8 (d, J = 194Hz). GCMS (EI): m/z = 119 [M – OH]+, 97 [M – CO2H]+. Anal. Calcd for C5H6F2O2: C, 44.13; H, 4.44. Found: C, 43.86; H, 4.42.

The chemical industry reduces the impact on the environment during synthesis Ethyl 3,3-difluorocyclobutanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Melnykov, Kostiantyn P.; Granat, Dmitriy S.; Volochnyuk, Dmitriy M.; Ryabukhin, Sergey V.; Grygorenko, Oleksandr O.; Synthesis; vol. 50; 24; (2018); p. 4949 – 4957;,
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. 294190-18-4, name is Methyl 3-amino-5-chloro-2-methylbenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-amino-5-chloro-2-methylbenzoate

[01341 ] Step 1 : Synthesis of methyl -chloro-3-(cycloheptylamino)-2-methylbenzoate[01 342] To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate ( 1 g, 5.02 mmol) and cycloheptanone (2.81 g, 25 mmol) in methanol (10 mL), acetic acid (0.3 g, 5.02 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.65 g, 10.05 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford 5- chloro-3-(cycloheptylamino)-2-methylbenzoate (0.8 g, 56.2 %).

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; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 431-47-0, name is Methyl 2,2,2-trifluoroacetate, 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 431-47-0, name: Methyl 2,2,2-trifluoroacetate

Example 7. Synthesis of a labeled compound of the present invention [a fluorescent labeling, 2′-deoxycytidine-5′-triphosphate derivative]; Mononucleotide (2′-deoxycytidine-5′-triphosphate) labeled with the compound [1] of the present invention was synthesized as follows according to the above-described synthesis route.(1) Synthesis of the partial linker (A); (i) Trifluoroacetylation (Tfa) (the first step); To 21 g of propagylamine, [the compound (51) in the above synthesis route], (manufactured by Tokyo Chemical Industry Co., Ltd.), methyl trifluoroacetate (MeOTfa) (54 g) and triethylamine (Et3N) (25 mL) were added, under ice-cooling, to be subjected to stirring at room temperature for 2 days. After completion of the reaction, purification was carried out under reduced pressure to give the compound (52), [the compound (52) in the above synthesis route], (56 g, yield; 98.1%).

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 2,2,2-trifluoroacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wako Pure Chemical Industries, Ltd.; EP2006289; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1732-08-7, name is Dimethyl pimelate, 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 1732-08-7, category: esters-buliding-blocks

Add 25000 ml of tetrahydrofuran to a 50-liter glass reactor and start stirring.Add 1500g lithium tetrahydroaluminate when cooling to 5C,Then, a mixture of 5000 g of dimethyl pimelate and 5000 ml of tetrahydrofuran was transferred to a dropping funnel.When the temperature of the reaction flask dropped to 5C, it began to be added dropwise.Control the temperature at 5 C, after the completion of the drop 1hThe mixture was slowly heated to room temperature and stirred for 1.5 hours. After the sample was taken, no raw material remained. It was qualified. The temperature was lowered to 5 C., and 1500 g of water, 1500 g of 15% sodium hydroxide solution, and 1500 g of water were added dropwise. The filtrate was concentrated to give 3360 g 1, Crude 7-heptanediol, crude 1,7-heptanediol was distilled under reduced pressure by an oil pump, and the oil bath temperature was 105C.The gas-phase collection temperature is 74C, giving 3201 g of 1,7-heptanediol,Content 99.6%, yield 95.3%;

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 pimelate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Haimen Huaxiang Pharmaceutical Technology Co., Ltd.; Wu Tiansheng; Zhou Guang; Xu Benquan; (5 pag.)CN107417496; (2017); 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. 6290-49-9, name is Methyl 2-methoxyacetate, A new synthetic method of this compound is introduced below., Product Details of 6290-49-9

Add 67.5g (1.25mol) to a 1000ml four-necked flaskSodium methoxide solid and 450ml of cyclohexane were heated to 50 C, and 52.0g (0.50mol) of methyl methoxyacetate was slowly added dropwise.Keep no more than 70 , about 1h dripping.Then keep the reaction at 80-90 for 16h. During this period, about 20ml of solvent was distilled off with water pump under reduced pressure every 3h, and 20ml of cyclohexane was added.The temperature was lowered to about 5 C, 6N hydrochloric acid was added to adjust pH = 6-7 (about 270ml), and then 200ml of water layer was added.The aqueous layer was extracted with cyclohexane (150 ml × 1), the organic layers were combined, washed with water (100 ml × 1), and decompressed under reduced pressure to obtain a brown liquid.Distillation under reduced pressure, collecting 114-115 C fraction (10 torr) to obtain intermediate III as a colorless transparent liquid, with a mass of 64.7 g, a yield of 73.7%, and a purity of 99.1%.

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; Nanjing Jieyun Pharmaceutical Technology Co., Ltd.; Zhou He; Shu Kai; Fang Jing; Zhang Li; Song Xingchang; Yu Zenghui; Wu Xiaodong; Liu Haomin; (10 pag.)CN111004121; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 51122-91-9, name is Dimethyl Isopropylmalonate, 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 51122-91-9, Application In Synthesis of Dimethyl Isopropylmalonate

Potassium hydroxide (32.2 g) and toluene (250 mL) were taken into a round bottom flask and stirred for about 10 minutes. Dimethylisopropyl malonate (50 g) and tetrabutylammonium bromide (10 g) were then added to it and again stirred for about 10 minutes, trans-lambda ,3-Dichloropropene (35 g) was added to the reaction mixture and maintained at about 30-35 C for about 4 hours. After the reaction was completed, the reaction mass was quenched with water (500 ml_) and stirred for about 10 minutes. The reaction mixture was extracted into toluene (250 ml_), and the toluene layer was washed with water and then evaporated under reduced pressure to afford 51 g (82% yield) of (£)-dimethyl 2- (3-chloroallyl)-2-isopropylmalonate as a dark brown viscous liquid. Purity by GC: 96.84%

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; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; APPAYE, Kaliyaperumal Srinivasan; GANGULA, Srinivas; GOVINDAPUR, Rajeshwar Reddy; MANNE, Nagaraju; NIKUMBH, Satish Pandurang; NEELAM, Uday Kumar; JOSEPH, Suju Chuttippari; BADDAM, Sudhakar Reddy; KUNHIMON, Shyam Kumar Unniaranpurakkal; MOOVENDAN, Mohan; DAHANUKAR, Vilas; DONIPARTHI, Kiran Kumar; WO2012/21446; (2012); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics