Esters-buliding-blocks

Some common heterocyclic compound, 1462-12-0, name is Diethyl 2-ethylidenemalonate, molecular formula is C9H14O4, 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. Product Details of 1462-12-0

General procedure: To a mixture of alkene 1 (0.5 mmol), aldehyde 2 (2.5 mmol), and FeCl2 (1.6 mg, 0.0125 mmol), acetonitrile (3.0 mL) was added under nitrogen at room temperature. Then tert-butyl hydroperoxide 3 (TBHP, 2.0 mmol, 5-6 M in decane) was dropped into the mixture under nitrogen at room temperature. The resulting mixture was stirred under 85 oC for 1 h. The temperature of reaction was cooled to room temperature. The resulting reaction solution was directly filtered through a pad of silica by ethyl acetate. The solvent was evaporated in vacuo to give the crude products. NMR yields are determined by 1H NMR using dibromomethane as an internal standard. Solvent was evaporated and the residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether as eluent to afford the pure product 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1462-12-0, its application will become more common.

Reference:
Article; Liu, Kaisheng; Li, Yuanming; Zheng, Xiaojian; Liu, Weiping; Li, Zhiping; Tetrahedron; vol. 68; 50; (2012); p. 10333 – 10337;,
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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 914943-91-2 as follows. SDS of cas: 914943-91-2

-Butyl 3-ethynyibenzoate (117) (1.603 g, 7.93 mmol), 4-iodo-2-(methylthio)-5- (trifiuoromethyl)pyrimidine (114) (1.647 g, 5.15 mmol), PdCI2(PPh3)2 (0.316 g, 0.45 mmoi), PPh3 (0.355 g, 1.35 mmol), Cu(i)i (0.232 g, 1.22 mmol) and trethyiamine (4.00 mL, 28.7 mmoi) were combined in D F (20 mL) and the resulting mixture heated at 120 C under microwave irradiation for 25 minutes. The mixture was then concentrated under reduced pressure and purified twice using silica gel column chromatography (10-20% EtOAc/petroleum benzine 40-60 C then 50-100% DCM/petroleum benzine 40-60 C) to give the title compound (118) (0.624 g, 31 %) as a yellow solid; 1H NMR (400 MHz, CDCI3) delta 8.73 (d, J = 0,8 Hz, H), 8.25 (m, H), 8.08 (m, 1 H), 7.78 (m, 1 H), 7.48 (m, 1 H), 2.63 (s, 3H), 1.61 (s, 9H).

According to the analysis of related databases, 914943-91-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
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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. 123-95-5, name is Butyl stearate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

An esterification reaction mixture (94 g), consisting of butanol (ca., 4.9% w/w), butyl stearate (95.1% w/w), residual stearic acid (trace), residual methanesulfonic acid catalyst (1383 ppm) and undesired butyl methanesulfonate (613 ppm) was treated with 45% aqueous KOH (229 mg, 1.84 mmol as compared to 1.74 mmol MSA originally charged to the reaction). The resulting mixture was heating at 50 C. for 40 minutes. Without wishing to be bound by any particular theory or explanation, it is believed that reaction of butyl stearate with KOH produced potassium stearate, which retains significant solubility in the butyl stearate medium. The formed potassium stearate then reacted with butyl methanesulfonate to produce potassium methanesulfonate and butyl stearate. After filtration of the by-product solid salts (0.6325 g), analysis of the mixture by gas chromatography revealed only 300 ppm unreacted butyl methanesulfonate, a 51% reduction. Repetition of the above KOH treatment at a higher temperature (175 C./60 min.) revealed complete reaction of the butyl methanesulfonate. Similarly, treatment with NaOH was found equally effective as treatment with KOH. Treatment with Ca(OH)2 proved ineffective, presumably due to formation of poorly soluble calcium salts. Treatment with acidic tin(II) or zirconium (IV) salts resulted in formation of additional butyl methanesulfonate.

The synthetic route of 123-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Smith, Gary; Cordova, Robert; Chen, Johnson C.H.; Chen, Mabel; US2006/30725; (2006); A1;,
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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 89901-03-1 as follows. SDS of cas: 89901-03-1

Example 97; (4′ -Bromo-biphenyl-4-yl) -methanol; A solution of 4′ -Bromo-biphenyl-4-carboxylic acid methyl ester, 7.8g (27.9′ mmol) in 15OmL of tetrahydrofuran was cooled to 0 0C via ice-water bath. Lithium aluminum hydride, l.lg (27.9 mmol) was added to the solution in one portion. The reaction mixture stirred at 0 0C for Ih. The mixture was slowly quenched with 1OmL of isopropyl alcohol, then with 1OmL of water. The aqueous mixture was extracted with 3x50mL portions of ethyl acetate. The organic layers were combined, washed with sat. aq. NaCl, and dried (MgSO4) . The solution was concentrated to afford the desired product in 7.01g (100%) as a white solid. The material was taken to the next step without further purification.

According to the analysis of related databases, 89901-03-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE INSTITUTES FOR PHARMACEUTICAL DISCOVERY, LLC; WO2006/55725; (2006); A2;,
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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. 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9BrO2

Degas a suspension of methyl 2-(2-bromophenyl)acetate (156.6 g, 684 Tnmoi), bis(inacoiato)diboron (194.9 g, 752 mmoi), and potassium acetate (135,6 g, 1.4 mol) in N-methylpyrroiidone (940 mL) with three vacuuni?nitrogen cycles, Add (1,1 bis(diphenyiphosphino)ferrocene)palladiurn(H) chloride (11,4 g, 13,7 nunol) and heat at 80C. After 15 hours add (1 , I -bis(diphenyiphosphino)ferrocene)palladiuni(II) chloride(11,4 g, 13.7 mmoi) and stir at 90 C for 24 hours, Cool to ambient tern perare and pour over a mixture of ice and water (3 L), and methyl tertiary butyl ether (1 L) was added, Stir mixture, filter through a pad of Celite and separate layers, Extract from aqueous with methyl tertiary hutyl ether (2×500 niL), Wash combined organics with water (2×500 mL), brine (500 mL), dry over sodium sulfate and concentrate. Purify the residue byflash chromatography, elating with hexane: ethyl acetate (9:1) to give the title compound as a white solid (160,6 g, 581.6 mrnol, 85%). MS (rn/z): 277(M+i),

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 57486-69-8.

Reference:
Patent; ELI LILLY AND COMPANY; BENHADJI, Karim A.; MASSARD, Christophe; SORIA, Jean-Charles; (43 pag.)WO2016/168014; (2016); A1;,
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Electric Literature of 139911-28-7, 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. 139911-28-7, name is Ethyl 2-bromo-5-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 2a. 8-fluorophenanthridin-6-ol.A mixture of methyl 2-bromo-5-fluorobenzoate (0.250 g, 1.07 mmol), 2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)aniline (0.235 g, 1.07 mmol), palladium acetate (2.4 mg, 0.01 eq.), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (8.81 mg, 0.021 mmol), and sodium carbonate (0.114 g, 1.073 mmol) in ethanol (5.4 mL) was heated to 80 C for 3 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was triturated with hexane, and isolated by vacuum filtration, washed with water, and dried to provide the title compound (0.15 g, 65% yield) which was used without further purification

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

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; ABBOTT LABORATORIES; MCDANIEL, Keith, F.; CHEN, Hui-ju; SHANLEY, Jason, P.; GRAMPOVNIK, David, J.; GREEN, Brian; MIDDLETON, Timothy; HOPKINS, Todd; OR, Yat, Sun; WO2012/92411; (2012); 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. 1731-79-9, name is Dimethyl dodecanedioate, A new synthetic method of this compound is introduced below., SDS of cas: 1731-79-9

1,12-dodecanedioic acid dimethyl ester (1000.0g, 3.87 mols) was put into a reactor, heated and stirred under a reduced pressure of 80kPa at 105C. Methanol was distilled off while the mixture of gamma-butyrolactone (83.3g, 0.97 mol) and 28% by weight of sodium methoxide solution in methanol (186.7g, 0.97 mols) prepared at the room temperature was dropped into the heated 1,12-dodecanedioic acid dimethyl ester in 30 minutes. After continuing the reaction for 30 minutes then, the pressure was reduced to 26.7 kPa to further continue the reaction for 240 minutes. Next, after returning to ordinary pressure, the reactant was cooled to 70C and, while being stirred, methyliodide (137.7g, 101.6 mols) was dropped into it in 30 minutes. N-hexane (700g) and, next, water (3009) were poured into it. After removing the water layer, it was washed with aqueous solution of 10% sodium hydroxide (150g: twice) and water (200.0g: twice). N-hexane was distilled off under a reduced pressure. The remained oily substance was subjected to a distillation under a reduced pressure (oil bath temperature 200C/60 to 130Pa) and excessive 1,12-dodecanedioic acid dimethyl ester was distilled off. 762.9g of a distilled substance and 264.2g of a distillation residue were obtained. As a result of an analysis of the distillation residue by gas chromatography, it was found that 80.7% by weight of the compound indicated by the general formula (2) (n = 10, R = Me) was contained. This was mixed with aqueous solution of 10% sodium hydroxide (675g) and heated/refluxed for 5.5 hours. After diethylene glycol (230g) and 60% hydrazine monohydrate (124g) were added to the reaction liquid and stirred for one hour at 110C, the temperature of the reaction system was elevated to 170 to 200C while removing water, and after aqueous solution of 30% sodium hydroxide (100g) was dropped into it in 4 hours, it was stirred for 6 hours at that temperature. While pouring water (930g) into it, it was cooled, and with addition of diluted sulfuric acid it was extracted with toluene. After the organic layer was washed with water, the solvent was removed under a reduced pressure, and 254g of a crystalline residue containing 13-methyl-15-hydroxypentadecanoic acid (n = 10) as the main component was obtained. This was cyclized by intramolecular ester interchange reaction to thereby obtain 80.7g of a cyclic compound. This contained 98.9% by weight of 13-methyl-15-pentadecanolide. The yield was 32 mol%/butyrolactone. 1H-NMR(CDCl3,400MHz) 4.16(2H)m; 2.32(2H)m; 0.90(3H)d J=6.4Hz 13C-NMR(CDCl3) 173.89; 61.86; 35.31; 34.49; 34.20; 30.82; 27.68; 27.25; 26.57; 26.42; 26.26; 26.10; 25.87; 24.89; 24.52; 19.51 IR(film) 2930; 2860; 1740; 1460; 1350; 1245; 1173; 1115 MS 254(5); 236(9); 225(11); 207(21); 111(16); 97(35); 83(42); 70(100); 55(68); 41 (40)

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; SODA AROMATIC COMPANY, LIMITED; EP1741706; (2007); A1;,
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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. 41727-48-4, name is Methyl 4-amino-3,5-dichlorobenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C8H7Cl2NO2

(i) Sodium nitrite (20 g) in water (50 ml) was added to a stirred mixture of methyl 4-amino-3,5-dichlorobenzoate (6.23 g) in concentrated sulphuric acid (110 g) and water (95 ml) at 0C. The mixture was stirred until all the solid had dissolved (overnight at 0C). To the stirred solution was added a solution of potassium iodide (25 g) in water at 50C and the resulting mixture was stirred at 20C overnight. The mixture was extracted with diethyl ether. The ethereal extracts were washed with aqueous sodium bisulphite solution and then dried over anhydrous magnesium sulphate. The solvent was evaporated in vacuo and the residue was chromatographed on silica, eluding with hexane: dichloromethane 7:3. 3.75 g of methyl 3,5-dichloro-4-iodobenzoate was obtained. Nuclear magnetic resonance spectrum (NMR) was as follows: ‘H (ppm from TMS in CDCl3, integral, number of peaks): 3.90, 3H, s; 7.95, 2H, s. Mass spectrum M+1 331.

The synthetic route of 41727-48-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE WELLCOME FOUNDATION LIMITED; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; EP279698; (1990); A3;,
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These common heterocyclic compound, 6642-30-4, name is Methyl methylcarbamate, 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. name: Methyl methylcarbamate

Step A 6-Cyanoindazole A solution of sodium nitrite (218 mg, 3.16 mmol) in water (1 mL) was added dropwise over 2 min to a stirred suspension of 3-amino-6-cyanoindazole (250 mg, 1.58 mmol) in water (1 mL) and acetic acid (2 mL) at 0 C. The resulting thick suspension was warmed to rt. After 16 h the mixture was cooled to 0 C. and the solids were collected by filtration, washing with cold water. The solids were suspended in 0.1 M HCl (4 mL), DME (3 mL) was added and the resulting mixture was stirred and heated to 80 C. for 1.5 h. The reaction was cooled and concentrated to 1/3 the volume. The residue was neutralised with sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography on silica (5:1 chloroform/ethyl acetate) to give the title compound as a yellow solid: LRMS=143.1 (M)+; 1H NMR (CDCl3) delta 7.39 (dd, J=1.1 and 8.3 Hz, 1H), 7.87 (dd, J=0.9 and 8.3 Hz, 1H), 7.94 (dd, J=0.9 and 2.1 Hz, 1H), 8.21 (d, J=0.9 Hz, 1H).

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

Reference:
Patent; Merck & Co., Inc.; US6376499; (2002); B1;,
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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 210530-71-5 as follows. Recommanded Product: Methyl 2-(3,4-difluorophenyl)acetate

Sodium hydride (containing mineral oil at 40%, 0.48 g) was added to a solution of methyl (3,4-difluorophenyl)acetate (CAS No.210530-71-5, 2.04 g) in DMF (30 mL) at 0 C., and the reaction solution was stirred at room temperature for 10 minutes. 1-chloro-3-iodopropane (1.3 mL) was added to the reaction solution at 0 C., and the reaction solution was stirred at room temperature for two hours. A saturated ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The resulting extract washed with a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. Hydrazine monohydrate (5.5 g) was added to a solution of the resulting residue in ethanol (50 mL) at room temperature, and the reaction solution was stirred at 80 C. for seven hours. The reaction solution was left to cool to room temperature and concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the residue, followed by extraction with chloroform. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 1.42 g of the title compound. The property values of the compound are as follows. ESI-MS; m/z 227 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.84-2.06 (m, 3H), 2.10-2.21 (m, 1H), 3.53-3.71 (m, 3H), 4.59 (brs, 2H), 6.89-6.95 (m, 1H), 6.97-7.05 (m, 1H), 7.06-7.26 (m, 1H).

According to the analysis of related databases, 210530-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/219181; (2007); A1;,
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