Tag: M.W=100-200

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. 63106-93-4, name is 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Phenyl-3-oxabicyclo[3.1.0]hexan-2-one

34 kg of aluminium chloride (255 moles) are suspended in 240 L of toluene and then 38.3 kg of diethylamine (523.5 moles) are added while maintaining the temperature between 15 and 300C. The lactone concentrate (38 kg) obtained earlier is poured on the medium maintained at 25C. The reaction medium is stirred for at least 1 hour 30 minutes. Formation of a precipitate is observed.This reaction medium is hydrolyzed with 345 L of water and then filtered after adding a filtration adjuvant. After decantation, the organic phase is washed twice with 235 L and 175 L of water and then concentrated until an amide-alcohol concentrate of 110 L is obtained.

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; PIERRE FABRE MEDICAMENT; NICOLAS, Marc; HELLIER, Paul; DIARD, Catherine; SUBRA, Laurent; WO2010/86394; (2010); A1;,
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Synthetic Route of 18448-47-0, These common heterocyclic compound, 18448-47-0, name is Methyl cyclohex-1-enecarboxylate, 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.

2.5 M n-Butyllithium in hexanes (7.25 mL, 18.1 mmol) was added dropwise to a cooled (ice water bath) mixture of S-(-)-N-benzyl-alpha-methylbenzylamine (15.1 mmol) in THF (60 mL). After stirring for 30 minutes the mixture was cooled to -95 C. (liquid nitrogen/acetone bath). A solution of methyl-1-cyclohexenecarboxylate (12.5 mmol) in THF (10 mL) was added to the chilled reaction mixture dropwise. After 1.5 hours the liquid nitrogen/acetone bath was replaced with a dry ice/acetone bath. The chilled reaction mixture was stirred for 2 hours and was quenched by the dropwise addition of 2,6-di-tert-butylphenol (25.2 mmol) in THF (20 mL). The reaction mixture was warmed to room temperature then concentrated in vacuo. The residue was dissolved in 100 mL of 50% dichloromethane in ether. The mixture was washed twice with brine. The organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. The crude material was purified by silica gel chromatography (solvent gradient: ethyl aceteate/hexanes, 2% to 5%) to afford the desired product (2.25 g) as a yellow oil in 54% yield.: 1H NMR (300 Mz, CDCl3) delta 7.38 (d, 4 H, J=7.3), 7.28 (m, 5 H), 7.18 (m, 2 H), 3.93 (m, 2 H), 3.77-3.68 (m, 1 H), 3.60 (s, 3 H), 2.68 (m, 1 H), 2.50 (m, 1 H), 2.14 (m, 1 H), 1.81 (m, 1 H), 1.70-1.52 (m, 4 H), 1.35-1.12 (m, 2 H) 1.27 (d, 3 H, J=7.0); MS m/e 352 (M+H)+.

Statistics shows that Methyl cyclohex-1-enecarboxylate is playing an increasingly important role. we look forward to future research findings about 18448-47-0.

Reference:
Patent; Marcin, Lawrence R.; Higgins, Mendi A.; US2005/113442; (2005); A1;,
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Electric Literature of 7270-63-5, 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. 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of diazo compound 1 (0.5 mmol) and alkynes (1.1 mmol) in toluene (2 mL) was added rhodium(II) pivalate (0.01 mmol). The reaction mixture was stirred at 60C for 0.5-5 h. The solvent was evaporated in rotary evaporator under reduced pressure to give the residue. The residue was purified by flash column chromatography on silica gel to give the product. 4.2.11. 2,4-Bis(3-chlorophenyl)-6H-furo[2,3-b]pyran-6-one (5j). Reaction of 1 (85 mg, 0.5 mmol) and 3-chloro-1-ethynylbenzene (149 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 5j (71 mg, 40%) as a solid: mp 198-200 C; 1H NMR (300 MHz, CDCl3) delta 7.57-7.56 (2H, m), 7.49-7.45 (4H, m), 7.31-7.19 (2H, m), 6.82 (1H, s), 6.16 (1H, s); 13C NMR (75 MHz, CDCl3) delta 159.1, 158.8, 152.2, 147.3, 136.7, 135.4, 135.1, 130.9, 130.6, 130.4, 130.2, 128.4, 127.5, 125.6, 123.6, 121.7, 105.7, 101.6, 99.4; IR (KBr) 3084, 1748, 1606, 1526, 1261, 1180, 1094, 785 cm-1; HRMS m/z (M+) calcd for C19H10Cl2O3: 356.0007. Found: 356.0007.

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, 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
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Adding a certain compound to certain chemical reactions, such as: 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, 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 4224-69-5, Computed Properties of C5H7BrO2

A 250 mL three-necked flask was evacuated with nitrogen to protect it, and the milled magnesium bars (2.06 g, 84.64 mmol) and THF (40 mL) were added in this order.Turn on stirring, heat to 45 ~ 55 C and add a piece of iodine under reflux to turn into a red-brown solution.The compound of formula 1 (9.2 g, 42.32 mmol) was dissolved in 26 mL of tetrahydrofuran,Then slowly add 20 drops to the reaction system,When the reaction system solution has a reddish brown color, it turns into a yellow emulsion until it turns into a white solution.As the reaction proceeds, the reaction system solution will become a clear and transparent liquid.After the addition, the reaction was performed for 0.5 h to obtain a compound of formula 2.; A 500 mL round-bottomed flask was evacuated with nitrogen, and the compound of formula 3 (5.00 g, 27.93 mmol),THF (80 mL), CuI (8.38 mmol, 1.60g) and LiCl (55.86 mmol, 2.37g),The reaction system was placed in an ice-water bath at 0 C.The compound of formula 2 obtained by the reaction was added dropwise to the reaction system. After the addition, the reaction was carried out for 0.5 h, and the reaction was moved to room temperature for 2 h.After the reaction was completed, an appropriate amount of water was added, followed by extraction with ethyl acetate (40 mL × 3) three times. The organic phases were combined, washed with saturated brine, and dried over anhydrous sodium sulfate.Suction filtration, the filtrate was concentrated under reduced pressure, the crude product was separated and purified by silica gel column (eluent: petroleum ether: ethyl acetate = 30: 1)The compound of formula 4 (5.39 g, yield 82%) was obtained as a colorless oily liquid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Shanxi Tumor Institute; Yang Xihua; Ou Wentao; (17 pag.)CN110776488; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 79909-92-5, 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 79909-92-5 as follows.

4-Amino-2,6-dimethyl benzoic acid (200 mg, 1.1 mmol) and NOBF4 (196 mg, 1.7 mmol) were heated in 1,2-dichlorobenzene at 100 C for 30 min. The solution was cooled and diluted with MeOH and water. A few pellets (2-3) of KOH were added, and the solution was heated at reflux for 16 h. The solution was concentrated. The residue was partitioned between Et2O and 1 N NaOH. The aqueous layer was extracted with Et2O. The aqueous layer was cooled to 0 C and acidified with conc. HCl (pH = 1-2). The aqueous layer was extracted with CH2Cl2. The organic layers were dried (Na2SO4). Filtration and concentration gave 58 mg (31 %) of the acid as a tan solid.

According to the analysis of related databases, 79909-92-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; EP1175401; (2005); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

1195768-18-3, name is Methyl 3-amino-2-fluorobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of Methyl 3-amino-2-fluorobenzoate

A stirred solution of methyl 3-amino-2-fluorobenzoate (7.32 g, 43.3 mmol) in pyridine (20 ml, 247 mmol) under argon was cooled in an ice-bath and treated portion-wise with 3,3,3-trifluoro-1 -propanesulfonyl chloride (10.0 g, 50.9 mmol) over 1 hour. The viscous orange-yellow mixture was magnetically stirred at room temperature overnight. The reaction mixture was partitioned between DCM and 4 M HCI (500 mL) and the separated organic phase was washed with water and brine (100 mL), dried (MgSO^, filtered andevaporated to obtain title compound (1 .82 g) a light purple solid.

The synthetic route of 1195768-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Jerry, Leroy; FAITG, Thomas; KASPAREC, Jiri; PENG, Xin; RALPH, Jeffrey; RHEAULT, Tara Renae; WATERSON, Alex Gregory; WO2011/59610; (2011); A1;,
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Ester – an overview | ScienceDirect Topics

Electric Literature of 35179-98-7,Some common heterocyclic compound, 35179-98-7, name is Chloromethyl ethyl carbonate, molecular formula is C4H7ClO3, 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 100 ml of one-necked flask, 0.698g of material, 0.162g of potassium carbonate, 5 ml of N,N-dimethylacetamide were added in turn. The solution was stirred at room temperature for 20 minutes. Then 0.702g of chloromethyl ethyl carbonate was added and the mixture was reacted at 45-50C for 16 hours. After the reaction was completed, the mixture solution was filtered, and 30ml of water was added into the filtrate. The resulting mixture was extracted with 30ml of ethyl acetate twice. The organic phase was dried and concentrated to give 1.854g of oil, which was directly used in the next reaction without purification. 10ml of dioxane and 5ml of 4mol/L HCl were added and the resulting mixture was reacted at room temperature for 16 hours. The reaction was stopped and the solution was adjusted to pH 6-7 using aqueous sodium bicarbonate solution. The solution went turbid, and was extracted with ethyl acetate. The organic phase was washed with saturated brine, dried, concentrated to give 0.420g of 2-butyl-4-chloro-1-[2′-(1H-tetrazol-5-yl)1,1′-biphenyl-methyl] imidazole-5- carboxylic acid, 1-[(ethoxycarbonyl)oxy] methyl ester. 1H-NMR (CDCl3) delta H (ppm) 0.92(t,3H,J=17.5), 1,23(t,3H,J=14.0), 1.37(m,2H,J=34.2), 1.73(m,2H,J=30.8), 2.69(t,2H,J=15.5), 4.13(q,2H,J=15.7), 5.58(s,2H), 5,89(s,2H), 6,99-7.61(8H), 8.16(d,1H,J=6.1) ESI(-): 539.1 Mp:164.5-160C

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

Reference:
Patent; SHANGHAI ALLIST PHARMACEUTICAL., INC.; EP1988090; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 15224-11-0, name is Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate, 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. HPLC of Formula: C7H12O3

Di-terf-butyl azodicarboxylate (4.8 g, 20.809 mmol) was added portionwise to a solution of 3-methoxy-5-nitrophenol [7145-49-5] (3.2 g, 18.917 mmol), ethyl 2-(hydroxymethyl)cyclopropanecarboxylate 6a (3 g, 20.809 mmol), and PP i3 (5.46 g, 20.809 mmol) in THF (150 mL). The reaction was stirred at room temperature under N2 for 18 h. The solution was concentrated under reduced pressure. The crude residue was purified by preparative LC (irregular SiOH 20-45 muetatauiota, 220 g, heptane/EtOAc from 85/15 to 75/25). The pure fractions were combined and concentrated under reduced pressure to give methyl 2-((3-methoxy-5- nitrophenoxy)methyl)cyclopropanecarboxylate 6b (1 .4 g).

The synthetic route of Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BONFANTI, Jean-Francois; KESTELEYN, Bart, Rudolf, Romanie; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; COESEMANS, Erwin; FORTIN, Jerome, Michel, Claude; MERCEY, Guillaume, Jean, Maurice; RABOISSON, Pierre, Jean-Marie, Bernard; (153 pag.)WO2018/215315; (2018); 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. 25081-39-4, name is Methyl 3,5-dimethylbenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H12O2

Methyl 3,5-bis[[bis(2-pyridylmethyl)amino]methyl]benzoate (3) Methyl 3,5-bis(bromomethyl)-benzoate (500 mg, 1.6 mmol) and di-(2-picolyl)-amine (800 mg, 725 muL, 4 mmol) were dissolved in ACN followed by the addition of dry K2CO3 (1.1 g, 7.9 mmol). The reaction mixture was refluxed overnight under reflux condenser equipped with a CaCl2 tube. The reaction mixture was filtered and filtrate was evaporated under reduced pressure. Yellow residue was purified by flash chromatography (Al2O3 neutral, firstly AcOEt was used to elute impurities and then MeOH/AcOEt=1:9 (v/v)) affording a pure product as a yellow oil. Yield: 850 mg (95%). 1H NMR (500 MHz, CDCl33) delta 8.51 (m, 4H), 7.94 (d, J=1.5 Hz, 2H), 7.70 (s, 1H), 7.61 (m, 8H), 7.12 (m, 4H), 3.92 (s, 3H), 3.81 (s, 8H), 3.73 (s, 4H). 13C NMR (101 MHz, CDCl3) delta 197.9, 167.1, 159.5, 148.9, 139.7, 136.2, 133.8, 130.2, 128.7, 122.8, 121.9, 60.1, 58.2, 52.0. MS (ESI, m/z): calculated: 558.7 observed: 559.5 [M+H]+.

The synthetic route of 25081-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Modpro AB; Baltzer, Lars; Slosarczyk, Adam; Bergquist, Jonas; Virtanen, Anders; (86 pag.)US9377466; (2016); B2;,
Ester – Wikipedia,
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Application of 3153-37-5,Some common heterocyclic compound, 3153-37-5, name is Methyl 4-chlorobutyrate, molecular formula is C5H9ClO2, 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 the product from step d (100 mg, 0.406 MMOL), K2CO3 (120 mg, 0.88 MMOL), Kl (cat.) and methyl 4-chlorobutyrate (140 mg, 1.02 MMOL) in acetone (2 ML) is heated at reflux for 8 hours. 1N sodium hydroxide (2 ML) is then added, and the mixture is heated at 60C for 2 hours. The reaction mixture is poured into water, acidified to pH 1 and then extracted with ethyl ether. The organic phase is washed with water and concentrated. Recrystallisation from cyclohexane of the residue obtained gives the expected product (40 mg). m. p. =81C 1H NMR-CDCI3- (PPM) : 0.87 (3H, m); 1.12-1. 43 (6H, m); 1.53 (2H, m); 2.09 (2H, m); 2.37-2. 68 (4H, m); 2.85 (2H, m); 3.23 (2H, m); 3.59 (2H, m); 4.03 (2H, m); 6.99 (1 H, s); 7.40 (1 H, s).

The synthetic route of 3153-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; WO2004/63148; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics