Category: esters-buliding-blocks

Reference of 32122-09-1, 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. 32122-09-1, name is Ethyl 2-(benzyloxy)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a reaction flask, lithium hexamethyldisilazide (LiHMDS, 1 M in toluene, 330 L, 0.33 mol) was charged followed by addition of anhydrous THF (400 mL). The solution was cooled down to -70 C. gamma-Butyrolactone (28.4 g, 0.33 mol) was added dropwise while the temperature of the reaction was kept at no more than 60 C. Ethyl benzyloxyacetate (50.0 g, 0.26 mol, formula XI, R1 = benzyl, R6 = ethyl) was added dropwise. After the addition, the reaction mixture was stirred at -60 C for 10 min. Ice-cold water (65 mL) was added, followed by addition of concentrated HCl to pH 3. The mixture was warmed to room temperature and the organic layer was collected. The aqueous layer was extracted with ethyl acetate (4×60 mL). The combined organic layers were evaporated and the residue was purified by flash column chromatography to afford 40.0 g (52% yield, based on gamma-butyrolactone) of a compound of formula II, wherein R1 is benzyl.

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, Ethyl 2-(benzyloxy)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lonza Ltd; The designation of the inventor has not yet been filed; EP2634180; (2013); A1;,
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Application of 3618-04-0, 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 3 : 8-(3-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)-lH-pyrazol-l-yl)-2- oxaspiro [4.5] decan-1-one; Step 1: ethyl 4-(tert-butyldimethyIsilyloxy)cyclohexanecarboxylate.; [124] tert-Butyldimethylsilyl chloride (3.61 g, 0.0240 mol) was added to a solution of 4- hydroxy-cyclohexanecarboxylic acid ethyl ester (3.44 g, 0.0200 mol; ), and lH-imidazole (3.40 g, 0.0499 mol; ) in N,N-Dimethylformamide (5.0 mL, 0.064 mol). The mixture was stirred at the room temperature for 3 hours. The mixture was partitioned between ethyl acetate and water. The ethyl acetate phase was washed with brine, dried over sodium sulfate, filtered, and then concentrated to give oily crude product. Column chromatography eluting with 0-20% ethyl acetate/hexanes gave 5.5 g (96%) of the title compound as colorless oil. 1H-NMR (300 MHz, CD3Cl) delta 4.12 (m, 2H), 3.72 (m, IH), 2.29 (m, IH), 1.93 (m, 2H), 1.65 (m, 2H), 1.56 (m, 2H), 1.48 (m, 2H), .125 (m, 3H), 0.88 (d, 6H), 0.03 (d, 6H).

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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; WO2009/9059; (2009); A1;,
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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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 3-amino-4-methylbenzoate

Methyl-3-amino-4-methyl benzoate (50 g), cyanamide (42 g) was added to ethanol (300 rnL) in a round bottom flask at 25-35C. Concentrated hydrochloric acid (21.2 mL) was added to the reaction mass in a drop-wise manner at 25-35C under nitrogen atmosphere. The reaction mass was heated to 80-85C and, stirred for 6 hours. Then thereaction mass was concentrated under vacuum at less than 50C, then cooled to25-35C. Water (350 mL) was added to the reaction mass, cooled to 0-5C and stirred for 15 mins. Aqueous sodium nitrate solution (51.5 gin 135 ml of DM water) was added to the reaction mass at 0-5C in 45 rnins. The precipitate formed was filtered, washed with DM water, acetone followed by methyl tert-butylether (MTBE), and dried undervacuum at 50-55C to provide the title compound (47.5 g).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 18595-18-1.

Reference:
Patent; LAURUS LABS PRIVATE LIMITED; CHAVA, Satyanarayana; GORANTLA, Seeta Rama Anjaneyulu; INDUKURI, Venkata Sunil Kumar; MOTURU, Venkata Rama Krishna Murthy; JAMJANAM, Srivardhana Rao; SELA, Venkata Purushottama Siva Prasad; WO2015/87343; (2015); A2;,
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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. 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, A new synthetic method of this compound is introduced below., Product Details of 75567-84-9

According to the following scheme, electrochromic compound 8 was synthesized.The flask was charged with the above intermediate 2-1 (3.92 g, 10 mmol), methyl 3- (4-bromophenyl) propionate (4.86 g, 20 mmol), sodium tert-butoxide (3.84 g, 40 mmol), palladium (67 mg, 0.3 mmol), and tri-tert-butylphosphonium tetrafluoroborate (261 mg, 0.9 mmol), and after purging with argon gas, ortho-xylene (40 mL) degassed with argon gas was added, And the mixture was heated and stirred at 115 C. for 3 hours. The reaction solution was returned to room temperature and filtered through Celite. Next, the filtrate was concentrated and purified by silica gel column chromatography (stationary phase: neutral silica gel, mobile phase: toluene) to obtain Intermediate 8-1 as a pale yellow solid (yield 5.23 g , Yield 73%).

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; RICOH COMPANY LIMITED; GOTO, DAISUKE; SAGISAKA, TOSHIYA; YAMAMOTO, SATOSHI; KANEKO, FUMINARI; INOUE, MAMIKO; YASHIRO, TOHRU; YUTANI, KEIICHIRO; NAGAI, KAZUKIYO; SHIMADA, TOMOYUKI; SHINODA, MASATO; (45 pag.)JP2016/138067; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate, 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 1245643-11-1, Safety of Methyl 3,4-diamino-5-bromobenzoate

A 3M aqueous solution of NaOH (11.6 mL; 34.8 mmol) was added to a mixture of intermediates 3a and 3b (4.08 g; 11.6 mmol) in EtOH (60 mL) and THF (60 mL). The reaction mixture was stirred at rt overnight and evaporated under vacuum. The residue was acidified with a 0.5 N aqueous solution of HC1 to give a precipitate. The solid was filtered off, washed with water, then diethylether and dried under vacuum to give 3.86 g (99%o, yellow solid) of intermediate 4.

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 3,4-diamino-5-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; JOUSSEAUME, Thierry, Francois, Alain, Jean; (114 pag.)WO2018/178280; (2018); A1;,
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Application of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, 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: A 50-mL glass reactor was charged under dry argon at 0 C with 15 mL of THF, and 20 mmol of magnesium powder, 20 mmol of EtAlCl2, and 1.0 mmol of Cp2TiCl2 were added in succession under stirring. After 1 h, 10 mmol of symmetrical acetylene and 20 mmol of ester were added, and the mixture was heated to 60 C and stirred for 6 h at that temperature. When the reaction was complete, the mixture was cooled to 0 C in a stream of argon, 10-15 mL of diethyl ether was added, and the mixture was hydrolyzed with 5 % aqueous HCl. The organic layer was separated, the aqueous layer was extracted with two portions of diethyl ether, and the combined extracts were washed with a solution of NaHCO3 until neutral washings and dried over MgSO4. The product was isolated by vacuum distillation.

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

Reference:
Article; Khafizova; Shaibakova; Chobanov; Gubaidullin; Tyumkina; Dzhemilev; Russian Journal of Organic Chemistry; vol. 51; 9; (2015); p. 1277 – 1281; Zh. Org. Khim.; vol. 51; 9; (2015); p. 1303 – 1307,5;,
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Reference of 87-13-8, 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. 87-13-8, name is Diethyl 2-(ethoxymethylene)malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Phenylaminomethylene-malonic acid diethyl ester: 2-(Ethoxymethylene)-malonic acid diethyl ester (50 mmol) and aniline (50 mmol) are mixed in a flask. The flask is sealed, and the mixture is heated to 1509C in a microwave reactor, stirred for 15 min and then cooled to rt. The crude oil is purified by flash-chromatography (cyclohexane / EtOAc 90 : 10) to yield the title compound in the form of a yellow, viscous oil.

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

Reference:
Patent; NOVARTIS AG; WO2009/21961; (2009); A1;,
Ester – Wikipedia,
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Some common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, molecular formula is C4H3BrO2, 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. Application In Synthesis of Methyl 3-bromopropiolate

d Methyl 5-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylselenyl)penta-2,4-diynoate In a manner similar to that of Example 35, the expected product is obtained by coupling 321 mg of methyl bromopropynoate and 200 mg of 6-ethynylselenyl-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene, in a yield of 28% (70 mg). 1H NMR/CDCl3: 1.23 (s, 6H); 1.33 (s, 6H); 1.67 (s, 4H); 2.35 (s, 3H); 3.79 (s, 3H); 7.13 (s, 1H); 7.65 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 23680-40-2, its application will become more common.

Reference:
Patent; Galderma Research & Development S.N.C.; US6444709; (2002); 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 57486-67-6 as follows. Safety of Methyl 2-(2-fluorophenyl)acetate

Example 1A Methyl 3-(3,5-dichloropyridin-2-yl)-2-(2-fluorophenyl)-3-oxopropanoate 28.5 ml (28.5 mmol) of a 1 M solution of LiHMDS in hexane are added to 50 ml of THF at -78 C. A solution of 4.00 g (23.8 mmol) of methyl (2-fluorophenyl)acetate in 10 ml of THF is then added dropwise. The mixture is stirred at -78 C. for 1 h and then 6.00 g (28.5 mmol) of 3,5-dichloro-pyridine-2-carbonyl chloride are added in portions. After a further hour, the mixture is allowed to reach RT and saturated ammonium chloride solution is added dropwise. The mixture is diluted with water and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution and dried over sodium sulfate. The residue after concentration in vacuo is purified by chromatography on silica gel (eluent: dichloromethane/methanol 50:1). 4.46 g (46% of theory) of the desired compound are obtained as a yellowish oil. LC/MS (Method 5): Rt=2.77, 2.82 min; MS (ESIpos): m/z=340 (35Cl2), 342 (35Cl37Cl), 344 (37Cl2) [M+H]+.

According to the analysis of related databases, 57486-67-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; US2010/29653; (2010); A1;,
Ester – Wikipedia,
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Application of 84228-44-4, The chemical industry reduces the impact on the environment during synthesis 84228-44-4, name is Methyl 4-amino-3-chlorobenzoate, I believe this compound will play a more active role in future production and life.

Reference Example 8 Methyl 4-amino-3-chlorobenzoate (5.65 g; synthesised in accordance with Synthesis, 1985, 669) was dissolved in tetrahydrofuran (112 ml) and admixed with a solution of sodium hydrogen carbonate (7.67 g) in water (84.8 ml) and benzyl chloroformate (39.1 ml) and the mixture was stirred under a nitrogen atmosphere at room temperature for 22.5 hours. The reaction mixture was extracted with ethyl acetate and the ethyl acetate layer was washed three times with water and then twice with saturated brine. The ethyl acetate layer was dried over magnesium sulfate and then the solvent was distilled off under reduced pressure, and then the residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1:7). A desired fraction was concentrated under reduced pressure and the residue was crystallized from a mixture of ethyl acetate and diisopropyl ether to yield methyl 4-benzyloxycarbonylamino-3-chlorobenzoate (7.51 g) as white crystals. 1H-NMR (CDCl3) delta: 3.91 (3H, s), 5.25 (2H, s), 7.38-7.44 (6H, m), 7.95 (1H, dd, J=8.8 Hz, 2.0 Hz), 8.06 (1H, d, J=2.0 Hz), 8.33 (1H, d, J=8.8 Hz).

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 4-amino-3-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6495604; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics