Month: June 2021

Synthetic Route of 1139-13-5,Some common heterocyclic compound, 1139-13-5, name is Diethyl cyclohexane-1,1-dicarboxylate, molecular formula is C12H20O4, 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. To a solution of compound 18-1 (4.0 g, 17.5 mmol) in EtOH (20 mL) was added 85% aqueous KOH solution (1.15 g, 17.5 mmol) at r.t. After the reaction mixture was stirred at 76 C for 3 h, it was concentrated and partitioned between EtOAc (15 mL) and H20 (25 mL). The aqueous phase was acidified with IN HC1 to pH = 3 and extracted with EtOAc (15 mL x 2). The organic layer was concentrated to give compound 18-2 as an oil (2.5 g, yield: 71.4%). ‘H NMR (400 MHz, CDC13) delta 4.20 – 4.15 (m, 2 H), 2.03 – 1.90 (m, 4 H), 1.56 – 1.47 (m, 6 H), 1.45 – 1.43 (t, 4.0 Hz, 3 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl cyclohexane-1,1-dicarboxylate, its application will become more common.

Reference:
Patent; GENENTECH, INC.; THE UNIVERSITY OF AUCKLAND; LEE, Ho Huat; TERCEL, Moana; FLYGARE, John A.; GUNZNER-TOSTE, Janet; PILLOW, Thomas H.; SAFINA, Brian; STABEN, Leanna; VERMA, Vishal; WEI, BinQing; ZHAO, Guiling; WO2015/95227; (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. 55666-43-8, name is tert-Butyl 3-bromopropanoate, A new synthetic method of this compound is introduced below., COA of Formula: C7H13BrO2

Description 8: 3- (4-Ethvl-2, 3-dioxo-piperazin-1-vl) propionic acid tert-butvl ester A suspension of 2-tert-butylimino-2-diethylamino-1, 3-dimethyl-perhydro-1, 3,2- diazaphosphorine on polystyrene (BEMP resin, loading 2. 3mmol/g, 0.54g) in acetonitrile (3ml) was treated with 1-ethyl-piperazine-2, 3-dione (0. 071 g) and tert- butyl-3-bromopropionate (0. 125g), and the mixture shaken at 22 for 16h. The resin was filtered off and washed with acetonitrile, and the filtrate and washings combined and evaporated in vacuo to give a white solid. The solid was applied in chloroform to a silica gel cartridge (Varian Bond Elut, 2g), and eluted sequentially with chloroform, ether, ethyl acetate and acetone. The acetone fraction was evaporated to give Description 8 as a white solid (0. 104g).

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2003/82863; (2003); A1;,
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Application of 26218-04-2, The chemical industry reduces the impact on the environment during synthesis 26218-04-2, name is 2-Ethylhexyl 4-aminobenzoate, I believe this compound will play a more active role in future production and life.

In a reactor, cyanuric chloride (18.4 g, 0.1 mole) is dissolved in 150 ml of acetone at 0 C.-5 C. Sodium bicarbonate (10.6 g, 0.1 mole) is added, then a solution of 2-ethylhexyl para-aminobenzoate (24.9 g, 0.1 mole) dissolved in 150 ml of acetone is added drop by drop at a temperature below 10 C. in 10 minutes. Next the heterogeneous mixture is left for 3 hours at laboratory temperature. 500 ml of water are poured in. The precipitate formed is filtered off, then washed with water. After drying under vacuum, 38 g of an off-white solid are obtained. After recrystallization of this solid from 1,2-dichloroethane, 25.2 g (yield 63%) of 2,4-dichloro-6-(2-ethylhexyl 4′-aminobenzoate)-s-triazine are obtained in the form of a white powder: UV (Ethanol/DMSO): lambdamax=291 nm, E1%=732, and used as such in the following stage.

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, 2-Ethylhexyl 4-aminobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; L’OREAL; US2008/8669; (2008); A1;,
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Electric Literature of 541-16-2, These common heterocyclic compound, 541-16-2, name is Di-tert-Butyl malonate, 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.

A mixture of di-tert-butyl malonate (4.3 g, 19.91 mmol, 1.99 equiv) and potassium carbonate (2.8 g, 20.29 mmol, 2.03 equiv) in N,N-dimethylformamide (30 mL) was stirred at 65C for 30 min. A solution of methyl 4-(4-(chloromethyl)-5-methyloxazol- 2-yl)benzoate (2.65 g, 10.00 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL) was then added dropwise with stirring to the reaction mixture. The resulting solution was stirred at 65C overnight and then quenched with 60 mL of ice and water. The mixture was extracted with 2×50 mL of ethyl acetate. The combined organic layers was washed with 3×30 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 4.0 g (90%) of methyl 4-(4-(3-tert-butoxy-2-(tert- butoxycarbonyl)-3-oxopropyl)-5-methyloxazol-2-yl)benzoate as a light yellow solid. LC-MS: (ES, m/z): 446 [M+H]+, 390, 334, 272, 230, 115.

The synthetic route of 541-16-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; RUGA CORPORATION; GIACCA, Amato; LAI, Edwin; RAZORENOVA, Olga; CHAN, Denise; HAY, Michael, Patrick; BONNET, Muriel; SUN, Connie; TABIBIAZAR, Ray; YUEN, Po-wai; WO2013/155338; (2013); 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. 24807-40-7, name is Methyl 3-(4-(benzyloxy)phenyl)propanoate, A new synthetic method of this compound is introduced below., Computed Properties of C17H18O3

To a solution of dimethyl methylphosphonate (1.16 g, 9.33 mmol) in THF (12.5 mL, 0.25 M) at -78 C was added nBuLi (3.9 mL, 9.33 mmol, 2.5 M in hexane). The mixture was stirred for 30 min after which a THF solution (2.5 mL) of ester 11 (750 mg, 3.10 mmol) was added slowly. The reaction mixture was warmed to RT and let stir for 1h, upon which time TLC indicated complete consumption of 11. The reaction mixture was quenched with saturated aqueous NH4Cl (5 mL). The mixture was diluted with H2O (10 mL) and extracted with EtOAc (4 x 25 mL). The combined organic layers were washed with H2O (50 mL), saturated aqueous NaCl (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. Purification by FCC (EtOAc) yielded 12 (1.09 g, 3.01 mmol, 97%) as a clear oil. Data for 12: Rf 0.45 (1:1 Hexanes: EtOAc); IR (thin film) 3034, 2955, 1714, 1512, 1244 cm-1; 1H NMR (700 MHz, CDCl3) delta 7.44 (d, J = 7.5 Hz, 2 H), 7.39 (t, J = 7.6 Hz, 2 H), 7.34 (t, J = 8.6 Hz, 2 H), 6.91 (d, J = 8.6 Hz, 2 H), 5.05 (s, 2 H), 3.76 (d, J = 11.3 Hz, 6 H), 3.08 (d, J = 22.7 Hz, 2 H), 2.94 (t, J = 7.2 Hz, 2 H), 2.87 (t, J = 7.2 Hz, 2H); 13C NMR (176 MHz, CDCl3) delta 201.1, 157.2, 137.1, 132.9, 129.4, 128.6, 127.9, 127.5, 114.9, 70.0, 53.1 (d, J = 6.3 Hz), 45.8, 41.6 (d, J = 128.0 Hz), 28.6; HRMS (ESI) calcd for C19H24PO5 [M+H]: 363.1357, found 363.1361.

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:
Article; Salih, M. Quamar; Beaudry, Christopher M.; Tetrahedron Letters; vol. 58; 21; (2017); p. 2023 – 2025;,
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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. 59247-47-1, name is tert-Butyl 4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of tert-Butyl 4-bromobenzoate

To a solution of (E)-styrylboronic acid (289 mg, 1.95 mmol) in mixed solution of dioxane and water (4:1, 15 mL) were added tert-butyl 4-bromobenzoate (500 mg, 1.95 mmol), tetrakis(triphenylphosphine)palladium (225 mg, 0.2 mmol) and sodium carbonate (622 mg, 5.9 mmol). The mixture was stirred at 90° C. under nitrogen atmosphere for 18 hours. Once start material has been consumed, the mixture was concentrated to give a residue and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=25:1) to give (E)-tert-butyl 4-styrylbenzoate (0.1 g, 18percent). The product was used for the next step directly without further purification.

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Constellation Pharmaceuticals, Inc.; Albrecht, Brian K.; Audia, James Edmund; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Nasveschuk, Christopher G.; US9206128; (2015); B2;,
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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. 1459-93-4, name is Dimethyl isophthalate, A new synthetic method of this compound is introduced below., Recommanded Product: Dimethyl isophthalate

In a 3-necked 500 mL round-bottomed flask equipped with a mechanical stirrer was placed dimethyl isophthalate (20.00 g, 0.103 mol, 1 eq.) dissolved in acetone (200 mL). To this mixture was added dropwise over 20 min a sln of NaOH (4.33 g, 0.108 mol, 1.05 eq.) in MeOH (40 mL). The resulting milky suspension was stirred at r.t. overnight. Then, another portion of NaOH (0.433 g, 0.011 mol, 0.1 eq.) was added into the reaction and the suspension was stirred for another 5 hours. The solvent was removed under vacuum and the white precipitate thus obtained was dissolved in water (400 mL). Concentrated HCl (15 mL) was added dropwise until pH~1. Then, the suspension was filtered; the collected precipitate was washed with water (4×100 mL) and dried under vacuum at 65C for 24 hours to give white solid 18.25 g. The obtained monomethyl isophthalate was used directly without further purification. In a 3 necked 500 mL round-bottomed flask equipped with a magnetic stirrer and a low temperature thermometer under a nitrogen atmosphere was placed monomethyl isophthalate (5.00 g, 0.027 mol, 1 eq.) dissolved in dry THF (125 mL). Then, this solution was placed in an ice-water bath and a solution of BH3?SMe2 (2M in THF, 70 mL, 0.14 mol, 5 eq.) was added dropwise slowly over 90 min to maintain the temperature in the solution below 7C. After another 15 min, the cooling bath was removed and the solution was allowed to reach ambient temperature. After 5 hours, the reaction was carefully quenched (strong gas evolution) with small pieces of ice while cooling in an ice-water bath. When the gas evolution ceased, brine (50 mL) was added and the resulting mixture was extracted with diethyl ether (3×100 mL). The combined organic extracts were washed with diluted bleach (50 mL, original solution 9.6% bleach diluted 10 times), brine (50 mL) and dried (MgSO4). The solvent was removed under vacuum to give an oil which contained a small amount of white precipitate. Diethyl ether (20 mL) was added and the solid was removed by filtration and washed with Et2O (2×10 mL). The filtrate was concentrated to yield a pale yellow oil (4.48 g). The crude oil was then purified by silica gel column chromatography (PE:EA, 4:1 to 7:3) to afford methyl 3-hydroxymethylbenzoate (2d) as colorless oil (3.77 g, 82%). Rf = 0.17 (EtOAc:PE = 1:4); 1H NMR (300 MHz, CDCl3), delta (ppm): 8.00 (s, 1H, HAr), 7.93 (dt, J = 7.7, 1.4 Hz, 1H, HAr), 7.61 – 7.51 (m, 1H, HAr), 7.40 (t, J = 7.7 Hz, 1H, HAr), 4.71 (s, 2H, OCH2), 3.89 (s, 3H, OMe).

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:
Article; Wang, Shuai; Lafont, Dominique; Rahkila, Jani; Picod, Benjamin; Leino, Reko; Vidal, Sebastien; Carbohydrate Research; vol. 372; (2013); p. 35 – 46;,
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These common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, 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 2,4-difluorobenzoate

Under a nitrogen atmosphere,1H-pyrrolo[2,3-b]pyridin-5-ol (1.0 g, 7.45 mmol), Methyl 2,4-difluorobenzoate (1.6 g, 9.31 mmol), Potassium phosphate (2.05g, 9.69mmol)Add to 20mL diglyme solution,The reaction solution was stirred at 115 C for about 10 h.Plate analysis until the starting material is completely reacted.The reaction solution was cooled to room temperature, then quenched with water and ethyl acetate.Collect organic phase,Purification by column chromatography gave a white solid product (1.3 g).The yield was 62%.

The synthetic route of Methyl 2,4-difluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Tajirui Bio-pharmaceutical Co., Ltd.; Wang Yihan; Liu Zhiqiang; (35 pag.)CN108658983; (2018); A;,
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Synthetic Route of 57486-67-6,Some common heterocyclic compound, 57486-67-6, name is Methyl 2-(2-fluorophenyl)acetate, molecular formula is C9H9FO2, 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.

Sodium hydride (1427 g, 35.7 mmoi) was added to a solution of methyl 2-(-fiuorophenyl)acetate(2 g, 1189 mmoi) in TIfF (20m1) at 0 C and allowed to stir at same temperature for 30 mi Methyliodide (5.21 ml, 83 mrnoi) was added dropwise and reaction mixture was stirred at RT for overnight. The reaction mixture was neutralized with saturated ammoniurn chloride and extracted with ethyl acetate (2x150m1). Combined organic phase was washed with brine, dried with anhydrous sodium sulfate and evaporated to give methyl 2-( -fluorophenyl)-2-methyipropanoate (1.5 g, 7.64 mrnol, 64.3 % yield) as oil.

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

Reference:
Patent; PI INDUSTRIES LTD.; SAXENA, Rohit; PANMAND, Deepak Shankar; JENA, Lalit Kumar; SRIVASTAVA, Khushboo; RAJU, Jella Rama; MANJUNATHA, Sulur G; SAMANTA, Jatin; GARG, Ruchi; AUTKAR, Santosh Shridhar; VENKATESHA, Hagalavadi M; GADAKH, Ramdas Balu; KLAUSENER, Alexander G. M.; POSCHARNY, Konstantin; (219 pag.)WO2018/116072; (2018); A1;,
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Synthetic Route of 148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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.

To a stirred solution of methyl 4-bromo-3-methylbenzoate (5g, 21.8 mmol) in dry 1 ,4- dioxane(100 ml_), were added dry Cs2CO3 (10.65 g, 32.7 mmol) and morpholine (2.3 g, 26 mmol). The mixture was degassed for 10 min. BINAP (0.67 g, 1.1 mmol) and palladium(ll)acetate (0.24 g, 1.1 mmol) were added under N2 and the resulting mixutre was refluxed for 15h. The reaction mixture was filtered through a pad of celite and the filtrate was evaporated. The crude product was purified by flash chromatography, affording the title compound as a yellow solid (4.3 g, 84%). 1H NMR (CDCI3, 400 MHz) delta 7.86-7.90 (m, 2H), 7.13-7.16 (d, 1 H), 3.98-4.0 (m, 4H), 3.91 (3H, s), 3.10-312 (m, 4H), 2.45 (3H, s). LC/MS (Method A): 236.0 (M+H)+. HPLC (Method B) Rt 2.24 min (Purity: 95.3%).

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
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