Category: esters-buliding-blocks

Reference of 40876-98-0, A common heterocyclic compound, 40876-98-0, name is Sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate, molecular formula is C8H11NaO5, 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: 6-hydroxypyrimidine-4-carboxylic acid 63.5 g (0.29 mol) sodium diethyloxalacetate and 30.2 g (0.29 mol) formamidine acetate were added to 24.1 g (0.6 mol) NaOH in 3.6 L water. The mixture was stirred overnight at RT. Then activated charcoal was added and the mixture was refluxed for 1 h. It was filtered off hot and after cooling acidified with aqueous hydrochloric acid. The solution was evaporated to dryness by rotary evaporation. The residue contained the desired product and was used in the next step without any further purification. Yield: 83.0 g

The synthetic route of 40876-98-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
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. 5445-17-0, name is Methyl 2-bromopropanoate, A new synthetic method of this compound is introduced below., SDS of cas: 5445-17-0

After dissolving 5 g (19.06 mmol) of triphenylphosphine in 15 ml of toluene, an aqueous solution of 0.32 g (1.90 mmol) of potassium iodide in 15 ml of distilled water and 3.2 ml (28.6 mmol) of methyl 2-bromopropionate were added thereto. And the mixture was stirred at 70 C for 20 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, basified (pH 9) with 10 N aqueous sodium hydroxide solution, and extracted with dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, filtered under reduced pressure, and distilled under reduced pressure. The obtained solid was washed with hexane and then filtered under reduced pressure and dried under reduced pressure to give 6.0 g (yield: 91%) of the title compound.

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; Hanmi Pharmaceutical Co., Ltd.; Lee, Kwang Okh; Jo, Myung Gi; (13 pag.)KR2015/77974; (2015); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 57381-62-1, name is Methyl 2-bromo-4-chlorobenzoate, 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 57381-62-1, name: Methyl 2-bromo-4-chlorobenzoate

In a 500 ml round-bottomed flask, 30 g (68.9 mmol) of the compound of formula C-1,17 g (68.2 mmol) of methyl 2-bromo-4-chlorobenzoate,1.6 g (1.38 mmol) of tetrakistriphenylphosphine palladium was added to 150 ml of tetrahydrofuran, mixed with 80 ml of an aqueous solution of 28.6 g (207 mmol) of potassium carbonate and refluxed for 24 hours. The impurities were removed using chloroform and water, and then anhydrous magnesium sulfate was added to remove moisture. The solution was filtered and then recrystallized using chloroform and ethanol to obtain 21.2 g (yield 65percent) of the formula C-2.

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

Reference:
Patent; LG Chemical Co.,Ltd; Kim, Su Yeon; Lee, Ho Yong; Jo, Sung Mi; (43 pag.)KR2016/2354; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 50893-36-2, These common heterocyclic compound, 50893-36-2, name is 1-Chloroethyl ethyl carbonate, 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 10 To a mixture of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-tetrazol-1-yl)phenyl]-2-imidazolidinone (0.61 g) and 1-chloroethyl ethyl carbonate (3.7 g) was added acetonitrile (1 ml), and the mixture was stirred for 38 hours at 95¡ã C. The reaction mixture was concentrated under reduced pressure. To the residue was added diisopropyl ether (10 ml), and the resulting powder was collected by filtration. The powder was subjected to ODS column chromatography (eluent: methanol/water=3/2). The elude was concentrated in vacuo. The residue was dissolved in water (10 ml), and lyophilized to give 1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-tetrazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[1-(ethoxy-carbonyloxy)ethyl]-1H-1,2,4-triazolium chloride (Compound 7,90 mg) as a white powder. 1H-NMR(d6-DSMO) delta: 0.97(3H,d,J=7 Hz), 1.21,1.22(3H,t,J=7 Hz), 1.79,1.80(3H, d,J=6 Hz), 3.62~4.23(6H,m), 4.65~5.10(3H,m), 6.69~6.82(2H,m), 6.94~7.04(1H,m), 7.26~7.38(2H,m), 7.90(4H,s), 9.23(0.5H,s), 9.27(0.5H,s), 10.08(1H,s), 10.72(0.5H,s), 10.82(0.5H,s).

The synthetic route of 50893-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6407129; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 454-31-9,Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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.

Into an 100-mL 3 -necked round-bottom flask was added a solution of 1 ,4- dibromobenzene (0.23 g, 0.99 mmol) in tetrahydrofuran (50 mL). The solution was placed under nitrogen and cooled to -78C. w-Butyllithium (0.4 mL,2.5 M) was added dropwise, and the resulting solution was stirred for 30 min at the same temperature. Ethyl 2,2-difluoroacetate(0.14 g, 1.1 mmol) was added dropwise to the mixture and the resulting solution was stirred for an additional 1 h at -78C. The reaction was quenched by the careful addition of hydrochloric acid (2.0 mL, 1.0 M). The mixture was extracted with ethyl acetate (2 x 10 mL), and the organic layers were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to afford l-(4-bromophenyl) 2,2-difluoroethan-l-one. GCMS calc’d for C8H5BrF20[M]+: 234, found 234.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHILDERS, Matthew Lloyd; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; KATZ, Jason David; PU, Qinglin; SCOTT, Mark E.; THOMPSON, Christopher F.; ZHANG, Hongjun; FALCONE, Danielle; TORRES, Luis; BRUBAKER, Jason; ZENG, Hongbo; CAI, Jiaqiang; DU, Xiaoxing; WANG, Chonggang; BAI, Yunfeng; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146490; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 457097-93-7, These common heterocyclic compound, 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate, 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.

(b) 4-Amino-3-chloro-5-trifluoromethoxy-benzoic acidmethyl ester The product of the previous step (200.0 mg, 0.74 mmol) was dissolved in a mixture of ACN (9.44 mL) and DMA (0.944 mL) at RT. To this stirred solution was added N-chlorosuccinimide (108.2 mg, 0.81 mmol). The resulting mixture was heated at 60 C. for 1 h, cooled to RT and partitioned between EtOAc (20 mL) and saturated sodium bicarbonate (4 mL). The organic layer was washed with saturated sodium bicarbonate (4 mL) and brine (4 mL), dried over sodium sulfate, filtered, and concentrated to give a yellowish oil, which was purified by silica gel chromatography (12 g silica gel, 0-40% EtOAc/hexanes) to give the title intermediate as a white solid (173.8 mg, 88% yield). Structure confirmed by NMR.

The synthetic route of 457097-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LONG, Daniel D.; MCKINNELL, Robert Murray; JIANG, Lan; LOO, Mandy; LEPACK, Kassandra; VAN ORDEN, Lori Jean; OGAWA, Gavin; HUANG, Xiaojun; ZHANG, Weijiang; US2013/115194; (2013); A1;,
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. 58677-05-7, name is Ethyl 2-amino-5-methylbenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 2-amino-5-methylbenzoate

a) 5-Methyl-2-methylaminobenzyl chloride hydrochloride Ethyl 2-amino-5-methylbenzoate was treated with dimethylsulfuric acid to give a N-methylated product. The N-methylated product was reduced using lithium aluminum hydride to give 5-methyl-2-methylaminobenzyl alcohol.

The synthetic route of 58677-05-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; US5082943; (1992); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 15568-85-1, These common heterocyclic compound, 15568-85-1, name is 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione, 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.

4-Methoxyaniline (1.27 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (1.82 g) were dissolved in 2-propanol (40 ml), and the solution was stirred at 50C for 2 hr. The solvent was removed by distillation under the reduced pressure, and the residue was washed with ether to give 5-[(4-methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dio xan-4,6-dione (1.98 g, yield 73%). 5-[(4-Methoxy-phenylamino)-methylene]-2,2-dimet hyl-[1,3]dioxan-4,6-dione (1.28 g) and biphenyl (5.2 g) were suspended in diphenyl ether (20 ml), and the suspension was stirred at 220C for one hr. The reaction mixture as such was purified by column chromatography with a methanol-chloroform system to give 6-methoxy-1H-quinolin-4-one (398 mg, yield 49%). 6-Methoxy-1H-quinolin-4-one (398 mg) was suspended in diisopropylethylamine (3 ml), phosphorus oxychloride (1 ml) was added to the suspension, and the mixture was stirred at 100C for one hr. Water was added to the reaction mixture under ice cooling, and the aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution. The organic layer was extracted with ethyl acetate, and the ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an acetone-chloroform system to give 4-chloro-6-methoxyquinoline (375 mg, yield 42%).

The synthetic route of 15568-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1724268; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 106-32-1,Some common heterocyclic compound, 106-32-1, name is Ethyl octanoate, molecular formula is C10H20O2, 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.

Ethyl octanoate (105 g, 0.61 mol) was dissolved in methanol (420 mL, 4 V) and stirred, then pumped into the coil with pump A at a rate of 5.6 g/min, sodium borohydride (33.86 g, 0.92 mol), EtONa (1.24g, 0.018mol) was dissolved in methanol (105mL, 1V) and pumped to a 240mL coil with pump B at a rate of 1.5g / min. The coil was immersed in a 40 C oil bath, and the outlet was sampled by HPLC. The system was subjected to quenching extraction in a 2 L four-necked flask and subjected to column chromatography to obtain 70 g of a product in a yield of 80%.

The synthetic route of 106-32-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kailaiying Pharmaceutical Group (Tianjin) Co., Ltd.; Hong Hao; Lu Jiangping; Zhang Enxuan; Liu Zhiqing; Zhang Tao; (21 pag.)CN110156549; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 39503-58-7, 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. 39503-58-7, name is Methyl 5-bromo-2-methoxy-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

The bromo derivative from above (44.5 g, 0.17 mol) was added in small portions to conc. H2SO4 (170 mL) and the mixture was stirred in an ice-salt bath until all SOLIDS DISSOLVED. CONC. HN03 (17 mL) was then added dropwise over 20 min and stirring continued for an additional hour in the ice bath. The reaction mixture was then slowly added to ice-water (2 L) and the precipitated yellow solid was collected by filtration. The solid was washed with water, NAHC03 solution and water again. After drying, the desired nitro derivative was obtained as an orange solid (36.8 g).

The chemical industry reduces the impact on the environment during synthesis Methyl 5-bromo-2-methoxy-4-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO KG; WO2004/65367; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics