Category: esters-buliding-blocks

Related Products 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.

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

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:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
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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. 217314-47-1, name is Methyl 3-amino-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 217314-47-1

To the solution of 1.57 g (8.7 mmol, 1 eq) 3-amino-5-methoxy-benzoic acid methyl ester (CAS 217314-47-1, can be prepared according to literature procedures) and 0.11 g (0.87 mmol, 0.1 eq) 4-dimethylaminopyridine in 18 ml THF is added the solution of 1.89 g (8.7 mmol, 1 eq) BOC-anhydride in 7 ml THF. The reaction mixture is stirred at rt over night. After dilution with EtOAc the mixture is washed with aqueous sodium bicarbonate and brine, dried over sodium sulfate, and the solvents are evaporated at reduced pressure. The residue is purified by chromatography on silica (flashmaster, hexane to hexane/EtOAc 7/3) to give 0.83 g (2.9 mmol, 34%) product as white solid.MS (LC/MS): 182=[M+H]+ 1H-NMR (400 MHz, CDCl3): 7.54-7.51 (m, 1H), 7.39 (br s, 1H), 7.29-7.28 (m, 1H), 6.59 (br s, 1H), 3.93 (s, 3H), 3.87 (s, 3H), 1.56 (s, 9H).

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; Betschart, Claudia; Lerchner, Andreas; Machauer, Rainer; Rueger, Heinrich; Tintelnot-Blomley, Marina; Veenstra, Siem Jacob; US2008/132477; (2008); A1;,
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Reference of 114312-57-1, A common heterocyclic compound, 114312-57-1, name is Ethyl 3-fluoro-2-methylbenzoate, molecular formula is C10H11FO2, 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.

Add ethyl 3-fluoro-2-methylbenzoate (5.1g, 28mmol) to the reaction flask,N-bromosuccinimide (5.6g, 31mmol),Benzoyl peroxide (0.34g, 1.4mmol) and CCl4 (30mL).Under the protection of nitrogen, the temperature of the reaction solution was raised to 82C and the reaction was stirred for 17 hours.After the reaction was completed, the reaction solution was cooled to room temperature, filtered, and the filter cake was washed with EtOAc (50 mL). The resulting filtrate was sequentially saturated sodium thiosulfate solution (100 mL×2),The citric acid solution (50 mL) and saturated brine (50 mL) were washed, dried over anhydrous sodium sulfate, filtered, and the filtrate was vortexed under reduced pressure.The obtained crude product was purified using silica gel column chromatography (eluent: PE/EA (v/v) = 10/1),The title compound was obtained as a light yellow oil (6.17g, 84%).

The synthetic route of 114312-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Luo Huichao; Ren Qingyun; Yin Junjun; Wu Chunlin; Fan Yuxin; Mo Yufeng; Zhang Yingjun; (102 pag.)CN111057074; (2020); A;,
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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. 685-88-1, name is Diethyl fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Diethyl fluoromalonate

To a solution of diethyl 2- fluoromalonate (5.00 g, 28.1 mmol) in EtOH (100 mL) was added LiOH H20 (2.70 g, 64.3 mmol) at 25 C. The mixture was heated to 50 C for 16 hours. The mixture was filtered to collect solid. The filtrate was concentrated to dryness to get oil. The oil and the solid were dissolved in H20 (30 mL) and MTBE (100 mL), the mixture was acidified by adding cone. HC1 to pH 1, the aqueous layer was extracted with MTBE (30 mL x2), the combined organic layers were dried over Na2S04, filtered and concentrated to give 2-fluoromalonic acid (3.00 g, yield 88%) as a solid.

According to the analysis of related databases, 685-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; QIU, Jian; STOUT, Adam; WO2012/83165; (2012); 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

Step 1. Preparation of methyl 1H-indazole-6-carboxylate (i-14b).Methyl 3-amino-4-methylbenzoate (i-14a) (5.0 g, 30.2 mmol) was dissolved in AcOH (140 mL). Sodium nitrite (2.1 g, 30.2 mmol) in water (3.5 mL) was added dropwise to the solution of starting material under ice-cooling at room temperature. The ice bath was removed and themixture was stirred overnight. Half of the solvent was evaporated, the mixture was diluted with water (80 mL) and extracted with EtOAc (3×30 mL). The collected organic phase was washed with water and brine (2×200 mL), dried and evaporated to afford the title compound (4.4 g), yield 83%. LCMS (ESI): calc?d for C9H8N202, [M+H]: 177, found: 177.

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; MERCK SHARP & DOHME CORP.; BARR, Kenneth Jay; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard Thomas; WO2014/28600; (2014); A2;,
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Electric Literature of 3618-04-0, The chemical industry reduces the impact on the environment during synthesis 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, I believe this compound will play a more active role in future production and life.

EXAMPLE 5 5-Butyl-9-[1-(4,6-dimethyl-pyrimidine-5-carbonyl)-4-methyl-piperidin-4-yl]-3-(trans-4-hydroxy-cyclohexylmethyl)-1-oxa-3,9-diaza-spiro[5.5]undecan-2-one (I-4) 4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38)-To a solution of 4-oxy-cyclohexanecarboxylic acid ethyl ester (CASRN 17159-80-7, 1.7 g, 0.01 mol) in DMF (14 mL) was added DMAP (58 mg, 0.47 mmol), TEA (1.54 mL) and tert-butyl-dimethylsilyl chloride (1.65 g, 0.011 mol). The reaction mixture was stirred at RT for 18 h, poured into ice (10 g), extracted with EtOAc (3*50 mL). The organic extracts were dried (MgSO4) filtered and concentrated. The residue was purified by SiO2 chromatography eluding with EtOAc/hexane (1:20) to afford 2.25 g (79%) of 4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38) as colorless oil.

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; Rotstein, David Mark; Melville, Chris Richard; US2008/249087; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 32122-09-1, name is Ethyl 2-(benzyloxy)acetate, 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 32122-09-1, Safety of Ethyl 2-(benzyloxy)acetate

To a solution of ethyl 2-(benzyloxy)acetate (1.30 g, 6.69 mmol) in anhydrous THF (30 mL) at -78 C was added dropwise LDA (2.0 M, 4.40 mL). The mixture was stirred for 30 min, and then tert-butyl 4-oxopiperidine-l-carboxylate (1.15 g, 5.77 mmol) in anhydrous THF (20 mL) was added. The mixture was stirred at -78 C for 1 hour, then quenched with sat aqueous H4CI (30 mL) and extracted with EtOAc (50 mLx3). The combined organic extracts were washed with brine and dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column (25% EtOAc in pet ether) to give the desired product as a colorless oil (1.82 g). Yield 80% (95% purity, UV=214 nm, ESI 294.1 (M+H)+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(benzyloxy)acetate, and friends who are interested can also refer to it.

Reference:
Patent; LAZULI, INC.; HARRISON, Bryce, Alden; BURSAVICH, Matthew, Gregory; GERASYUTO, Aleksey, Lgorevich; HAHN, Kristopher, Neil; KONZE, Kyle, David; LIN, Fu-Yang; LIPPA, Blaise, Scott; LUGOVSKOY, Alexey, Alexandrovich; ROGERS, Bruce, Nelsen; SVENSSON, Mats, Ake; TROAST, Dawn, Marie; (0 pag.)WO2018/160522; (2018); A1;,
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Electric Literature of 154825-97-5, 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. 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: Preparation of 2-(4-Bromophenyl)-2-methylpropanoic acid; [0525] A solution of methyl 2-(4-bromophenyl)-2,2-dimethylacetate(3880 muL, 15090 mumol) in EtOH (80 mL) and water (20 mL) was treated with KOH (4233 mg, 75450 mumol). The reaction was heated to 900C. After 15 hours, the reaction was cooled to 23C and concentrated in vacuo. The crude mixture was partitioned between water/diethyl ether (150 mL each). The aqueous layer was separated and extracted with diethyl ether (100 mL). The combined ether layers were then extracted with a IN NaOH solution (25 mL). The combined aqueous washes were acidified with concentrated HCl to pH = 2.0 and extracted with EtOAc (3 x 100 mL). The combined EtOAc layers were dried over MgSO4, and concentrated in vacuo to afford 3144 mg of 2-(4- bromophenyl)-2-methylpropanoic acid.

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-(4-bromophenyl)-2,2-dimethylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; WO2008/76427; (2008); A2;,
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Electric Literature of 99548-54-6,Some common heterocyclic compound, 99548-54-6, name is Methyl 3-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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 110 methyl { (3S) -6- [ (3-bromo-2-methylbenzyl) amino] -2, 3-dihydro-l- benzofuran-3-yl } acetate; [0990][0991]Methyl 3-bromo-2-methylbenzoate (2.29 g, 10.0 mmol) was dissolved in tetrahydrofuran (50 mL) , under ice-cooling, lithium aluminum hydride (0.285 g, 7.50 mmol) was added by small portions, and the mixture was stirred under a nitrogen atmosphere for 2 hr. Sodium sulfate 10 hydrate (2.42 g, 7.50 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr. Insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The obtained solid was recrystallized from heptane-ethyl acetate to give 3-bromo-2-methylbenzyl alcohol (1.76 g, yield 88%) as colorless crystals. This product (0.943 g, 4.69 mmol) was dissolved in acetonitrile (25 mL) , a Dess-Martin reagent (2.39 g, 5.63 mmol) was added by small portions under ice-cooling, and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was treated with saturated aqueous sodium hydrogen carbonate and aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A solution of the obtained colorless oil, methyl [ (3S) -6-amino-2, 3-dihydro-l- benzofuran-3-yl] acetate (0.972 g, 4.69 mmol) and acetic acid(0.537 mL, 9.38 mmol) in acetonitrile (25 mL) was stirred under a nitrogen atmosphere at room temperature for 0.5 hr. Sodium triacetoxyborohydride (1.99 g, 9.38 mmol) was added to the reaction mixture, and the mixture was further stirred for 12 hr. The reaction mixture was treated with water and saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate rhexane = 5:95-40:60) to give the title compound (1.59 g, yield 87%, 2 steps) as a colorless oil.1H NMR (300 MHz, CDCl3) delta 2.42 (3H, s) , 2.48-2.59 (IH, m) , 2.68-2.78 (IH, m) , 3.68-3.83 (4H, m) , 3.89 (IH, br s) , 4.18- 4.30 (3H, m) , 4.71 (IH, t, J = 9.1 Hz), 6.07-6.16 (2H, m) , 6.93 (IH, d, J = 8.0 Hz), 7.01 (IH, t, J = 7.9 Hz), 7.23-7.30(IH, m) , 7.49 (IH, dd, J = 7.9, 1.1 Hz). MS m/z 390 (M + H)+.

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-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; NEGORO, Nobuyuki; TERAO, Yoshito; MIKAMI, Satoshi; YUKAWA, Tomoya; WO2010/143733; (2010); A1;,
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Reference of 1215205-50-7, 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 1215205-50-7 as follows.

Step 4: 1-[4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclopropanecarboxylic acid ethyl ester 1-(4-Bromo-phenyl)-cyclopropanecarboxylic acid ethyl ester (3 g, 13.mmol), bis(pinacolato)diboron (3.37 g, 16.1 mmol), and potassium acetate (2.8 g, 29.0 mmol) were combined in 1,4-dioxane (30 mL) under N2. The solution was purged with N2 for 10 minutes, then (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.50 g, 0.65 mmol) was added and the reaction was heated to 80 C. for 2 hours. After aqueous workup, the crude material was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound.

According to the analysis of related databases, 1215205-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amira Phamaceuticals, Inc.; US2011/82181; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics