Author: tianli

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.2919-23-5, name is Cyclobutanol, molecular formula is C4H8O, molecular weight is 72.1057, as common compound, the synthetic route is as follows.Computed Properties of C4H8O

a) 5-Bromo-6-cyclobutoxy-3-pyridinecarboxylic acid 5-Bromo-6-chloro-3-pyridinecarboxylic acid (CAN 29241-62-1, 2.0 g, 8.46 mmol) was dissolved in DMSO (20.0 mL). Cyclobutanol (793 mg, 857 ??, 11.0 mmol) and potassium hydroxide powder (1.42 g, 25.4 mmol) were added and the mixture was stirred at room temperature overnight. Water (20 mL) was added and the mixture was acidified (under ice-water bath cooling) with 37% HC1 in water (pH = 2). The suspension was filtered, washed with water and the solid was dried to yield 1.88 g (82%) of the title compound as a white solid; MS (ESI): 270.2 (M-H)~. b) 5-(4-Chloro-phenyl)-6-cyclobutoxy-3-pyridinecarboxylic acid

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2919-23-5, Cyclobutanol, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GRETHER, Uwe; HEBEISEN, Paul; MOHR, Peter; RICKLIN, Fabienne; ROEVER, Stephan; WO2013/37703; (2013); A1;,
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Application of 62285-58-9 ,Some common heterocyclic compound, 62285-58-9, molecular formula is C9H12O, 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 solution of 2,6-dimethylbenzyl alcohol (456 mg, 3.35 mmol) and triethylamine (0.560 mL, 4.02 mmol) in dichloromethane (CH2Cl2, 15 mL) was added methanesulfonyl chloride (0.258 mL, 3.68 mmol) under ice-cooling and the mixture was stirred for one hour. Thereto was subsequently added lithium bromide (LiBr, 582 mg, 6.70 mmol) under ice-cooling, and the mixture was warmed to room temperature and the mixture was stirred for 2 hours. Thereto was added water to quench the reaction and the reactant was extracted with ethyl acetate and the organic layer was washed twice with water. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound 364 mg as colorless oils. 1H-NMR delta (DMSO-d6); 2.37 (6H, s), 4.71 (2H, s), 7.04-7.16 (3H, m).

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. 62285-58-9, (2,6-Dimethylphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1736467; (2006); A1;,
Alcohol – Wikipedia,
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Synthetic Route of 2077-19-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.2077-19-2, name is 2-(4-Bromophenyl)propan-2-ol, molecular formula is C9H11BrO, molecular weight is 215.09, as common compound, the synthetic route is as follows.

Example 2: Synthesis of 1-bromo-4-(1-methoxy-1-methyl-ethyl)-benzene:A mixture of 6.87 g of ethyl 4-bromobenzoate (10) was allowed to react with 64 mL(1.4 M in toluene) of methyl magnesium bromide in THF at -4O0C for 1 hour, and the reaction mixture was gradually warmed to O0C. The reaction was quenched with saturated aqueous ammonium chloride solution and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with brine, was dried over magnesium sulfate, was filtered, and the solvent was removed in vacuo. Purification by silica gel chromatography (50:1 to 10:1 EPO hexanes-ethyl acetate) afforded 6.44 g (99% yield) of 2-(4-bromophenyl)propan-2-o1 ; MS (AP/CI) observed: 199.1 (M+H – H2O)+, 100%; 213.1 , 215.1 (M-H)”, 60%, 80%. 2-(4- Bromophenyl)propan-2-o1 (1.77 g) and iodomethane (1.16 g) in THF (100 mL) were treated with sodium hydride, 60% in mineral oil (328 mg). After stirring for 24 h at room temperature, the reaction mixture was quenched with dilute aqueous hydrochloric acid, was extracted with ethyl acetate, and the organic layer was washed with brine, was dried over magnesium sulfate, was filtered, and the solvent was removed in vacuo. The resultant oil was purified by silica gel chromatography (200:1 hexanes-ethylacetate) to afford 0.5 g of 1-bromo-4-(1- methoxy-1-methyl-ethyl)-benzene; 13C NMR (400 MHz, CDCI3) delta 145.35, 131.53, 127.91 , 121.00, 50.90, 28.60.

Statistics shows that 2077-19-2 is playing an increasingly important role. we look forward to future research findings about 2-(4-Bromophenyl)propan-2-ol.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2006/75226; (2006); 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. 1777-82-8, name is (2,4-Dichlorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C7H6Cl2O

General procedure: Under an air atmosphere, a Schlenk tube was charged with MCM-41-bpy-CuI (40 mg, 0.025 mmol), alcohol (0.5 mmol), TEMPO (4 mg, 0.025 mmol), aqueous ammonia (0.5 mmol, 25e28%, w/w) and EtOH (1.0 mL). The mixture was stirred at 50 C for 18-48 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), and filtered. The MCM-41-bpy-CuI complex was washed with EtOH (2*5 mL), and Et2O (5 mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (petroleum/ethyl acetate=15:1 to 10:1) to provide the desired product.

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, 1777-82-8, (2,4-Dichlorophenyl)methanol.

Reference:
Article; Zhao, Hong; Chen, Qiurong; Wei, Li; Jiang, Yuanyuan; Cai, Mingzhong; Tetrahedron; vol. 71; 46; (2015); p. 8725 – 8731;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride, 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, 68327-04-8, blongs to alcohols-buliding-blocks compound. name: (1S,2S)-2-Aminocyclopentanol hydrochloride

150 mg (0.56 mmol) 3-(1-benzofur-2-yl)-6-chloroimidazo[1,2-b]pyridazine and 183.7 mg (1.34 mmol) (1S,2S)-2-aminocyclopentanol hydrochloride (1:1) and 186.9 mg (2.23 mmol) sodium hydrogencarbonate in 5.0 mL butan-1-ol were stirred 72 h at 150C. The solvent was removed. The residue was purified by HPLC to yield 29 mg (16%) of the compound. LC-MS (Method 2): Rt = 0.93 min; MS (ESIpos) m/z = 335 [M+H]+. 1H-NMR (300 MHz ,DMSO-d6), delta [ppm]= 1.47-1.91 (5H), 2.18-2.32 (1H), 3.92-4.01 (1H), 4.08-4.15 (1H), 4.78-4.82 (1H), 6.73-6.79 (1H), 7.10-7.16 (1H), 7.20-7.32 (2H), 7.56-7.66 (2H), 7.74-7.82 (2H), 7.88-7.92 (1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,68327-04-8, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ZORN, Ludwig; EIS, Knut; SCHULZE, Volker; SUeLZLE, Detlev; PUeHLER, Florian; LIENAU, Philip; BOeMER, Ulf; PETERSEN, Kirstin; HAeGEBARTH, Andrea; WO2014/76162; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.124-68-5, name is 2-Amino-2-methyl-1-propanol, molecular formula is C4H11NO, molecular weight is 89.1362, as common compound, the synthetic route is as follows.HPLC of Formula: C4H11NO

Example 24d 2-amino-6-(2-amino-2-methylpropoxy)benzonitrile To a solution of 2-amino-2-methylpropan-1-ol (14.4 g, 161 mmol) in anhydrous THF (150 mL) was added NaH (6.8 g, 161 mmol, 60% in mineral oil) in small portions at 0 C. under nitrogen. The mixture was stirred at 0 C. for 30 minutes and then stirred at room temperature for another 30 minutes. The solution was cooled down to 0 C. again, and to this solution was added dropwise a solution of 2-amino-6-fluorobenzonitrile (20.0 g, 147 mmol) in anhydrous THF (50 mL). The reaction mixture was then refluxed overnight under nitrogen. The reaction mixture was cooled down to room temperature and carefully quenched with aqueous NH4Cl solution and extracted with ethyl acetate (3*). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude mixture was purified by chromatography on silica gel eluting with 10% MeOH in DCM to give the title compound as yellow solid (23.4 g 71%). 1H NMR (400 MHz, DMSO-d6) delta 1.08 (s, 6H), 3.15 (s, 2H), 3.64 (s, 2H), 5.98 (s, 2H), 6.13 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.4 Hz, 1H), 7.15 (t, J=8.4 Hz, 1H). MS 236 (MH+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,124-68-5, 2-Amino-2-methyl-1-propanol, and friends who are interested can also refer to it.

Reference:
Patent; SENOMYX, INC.; US2012/41078; (2012); A1;,
Alcohol – Wikipedia,
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Application of 2568-33-4, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 2568-33-4, name is 3-Methylbutane-1,3-diol. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of allene 14 (101 mg, 0.288 mmol), DMF (0.3 mL) and 3-methyl-1,3-butanediol 28 (0.16 mL, 1.47 mmol) at 0 C were added (IPr)AuCl (18.0 mg, 0.030 mmol), AgOTf (8.0 mg, 0.031 mmol) and NIS (71.0 mg, 0.316 mmol). The reaction mixture was stirred for 22 h at 0 C, after which the mixture was diluted with Et2O, filtered through a plug of silica, washed with water and brine and dried (MgSO4). The product was isolated using flash column chromatography (2:1 hexane/diethyl ether) as a colourless oil (82.3 mg, 0.142 mmol, 49%). Stereochemistry of alkene was confirmed through NOE. Rf=0.38 (1:2 hexane/diethyl ether). numax/cm-1 3454 br (OH), 1631 w (CC), 1590 w, 1472 m, 1427 m (Ar CC), 1111 s (Si-O), 1088 s (C-O); 1H NMR (200 MHz, CDCl3) delta 7.49 (10H, m, Ar-H), 5.89 (1H, t, J 6.4, CH), 3.76 (2H, t, J 6.3, SiOCH2), 3.44 (2H, t, J 5.9, OCH2), 2.49 (2H, td, J 6.3, 6.4, CH2CHC), 1.75 (2H, t, J 5.9, OCH2CH2CMe2OH), 1.44 (6H, s, CH3), 1.25 (6H, s, CH3), 1.05 (9H, s, CH3). 13C NMR (50 MHz, CDCl3) delta 135.5 (CH), 133.7 (C), 133.6 (CH), 129.7 (CH), 127.7 (CH), 120.7 (C), 78.6 (C), 70.6 (C), 62.2 (CH2), 59.9 (CH2), 41.6 (CH2), 40.5 (CH2), 29.4 (CH3), 26.9 (CH3), 26.8 (CH3), 19.2 (C). [M+NH4]+=598.2202 (calcd for C28H41IO3Si+NH4+=598.2208).

According to the analysis of related databases, 2568-33-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Heuer-Jungemann, Amelie; McLaren, Ross G.; Hadfield, Maximillian S.; Lee, Ai-Lan; Tetrahedron; vol. 67; 9; (2011); p. 1609 – 1616;,
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Application of 13330-96-6, 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. 13330-96-6, name is 4-(Dimethylamino)butan-1-ol. A new synthetic method of this compound is introduced below.

General procedure: To a solution of 8 (1.00 mmol) in iPrOH (30 mL) was addedB2Pin2 (1.01 g, 4.00 mmol) and KOtBu (0.028 g, 2.50 mmol). Thereaction was stirred at 110 C. After 12 h, the mixture was cooled toroom temperature and was concentrated in vacuo. Then themixture was diluted with water and extracted with ethyl acetate.The combined organic layer was washed by saturated sodiumchloride solution for three times, dried over anhydrous Na2SO4 andconcentrated under reduced pressure. The residue was purified bysilica gel chromatography to give 9.To a stirred solution of 9 (0.29 mmol) and triphosgene (0.086 g,0.33 mmol) in anhydrous dichloromethane (5 mL) at 0 C wasadded triethylamine (0.12 mL, 0.87 mmol) under nitrogen atmosphere.Then a solution of 4-(dimethylamino)butan-1-ol(0.87 mmol) in dichloromethane (5 mL) was added. The mixturewas stirred at room temperature overnight, diluted withdichloromethane (15 mL) and washed with water (3 20 mL). Theorganic phases were separated, combined, dried over anhydrousNa2SO4 and concentrated in vacuo. The residue was purified byusing column chromatography to afford the corresponding product10a-10e.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13330-96-6, its application will become more common.

Reference:
Article; Lu, Dong; Liu, Jianan; Zhang, Yunzhe; Liu, Feifei; Zeng, Limin; Peng, Runze; Yang, Li; Ying, Huazhou; Tang, Wei; Chen, Wuhong; Zuo, Jianping; Tong, Xiankun; Liu, Tao; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 328 – 337;,
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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. 6850-65-3, name is 4-Aminocyclohexan-1-ol(isomers mixture), the common compound, a new synthetic route is introduced below. category: alcohols-buliding-blocks

To a microwave reactor vessel is added 4-(2,3- dimethoxyphenyl) -2-fluorobenzonit?le (0.23 g, 0.89 mmol) , 4- hydroxylcyclohexylamine (0.21g, 1.79 mmol), N, N- diisopropylethylamme (0.23 g, 1.79 mmol), and DMSO (2 mL) . The mixture is microwaved at 150 0C for 1500 sec with high absorbance. The mixture is extracted with ethyl acetate (100 mL) , washed with brine (2 X 50 mL) , and dried over MgSO4. The crude product is purified by a silica gel column with chloroform/methanol (95:5) as the eluent, affording 0.17 g of the desired 4- (2, 3-Dimethoxyphenyl) -2- (4- hydroxylcyclohexylamino) benzonitrile (54%) as a white solid. LCMS m/z = 353 [M+H] .

The synthetic route of 6850-65-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERENEX, INC.; WO2008/24963; (2008); A1;,
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Related Products of 3319-15-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 3319-15-1, name is 1-(4-Methoxyphenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The catalytic reactions were performed in a 10-mL autoclave reactor with an internal Teflon insert. Typically, 0.5 mmol of secondary alcohols, 0.04 mmol of Cu(OAc)2 and 0.04 mmol of ligand, 1 mmol of base, and 2 mL of solvent were added to the reactor.Then, the reactor was charged with 0.4 MPa O2 and heated to the desired temperature under magnetic stirring. When the reaction reached completion, the reaction mixture was diluted with 4 mL of methanol, and the catalyst was separated via centrifugation.The acid product was esterified with addition of 40 mul of BF3OEt2 at 100 C for 6 h in Ar atmosphere. In reaction condition optimization experiment, the products were identified and quantified using gas chromatography-mass spectrometry (GC-MS) and an Agilent7890A/5975C instrument equipped with an HP-5 MS column (30 m in length, 0.25 mm in diameter). p-Xylene was used as the internal standard. In the substrate scope experiment, the product was isolated and identified by NMR. The procedure for the isolation of the product is as follows: after the reaction completed, the reactor was cooled to room temperature in water and vented the gas.The reaction mixture was acidified with HCl 1.0 M (pH 1-2,15 mL) and then extracted with Et2O (3 x 20 mL). Next, the combined organic layers were washed with HCl 1.0 M (pH 1-2,3 10 mL), dried over anhydrous Na2SO4, and filtered and the Et2O was rotary evaporated. Solid products obtained were vacuum dried for 10 h at 60 C.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 3319-15-1, 1-(4-Methoxyphenyl)ethanol.

Reference:
Article; Wang, Min; Lu, Jianmin; Li, Lihua; Li, Hongji; Liu, Huifang; Wang, Feng; Journal of Catalysis; vol. 348; (2017); p. 160 – 167;,
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