Category: alcohols-buliding-blocks

Electric Literature of 873-76-7 , The common heterocyclic compound, 873-76-7, name is (4-Chlorophenyl)methanol, molecular formula is C7H7ClO, 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.

General procedure: p-Nitrobenzyl alcohol (0.25 g, 1.63 mmol) was dissolved in anhydrous CH2Cl2 under N2. Triethylamine (0.227 mL, 1.63 mmol) was added and the resulting solution was cooled to 0 C. S2Cl2 (65.3 muL, 0.82 mmol) was added dropwise over twenty minutes. The solution was stirred at 0 C for two hours before being allowed to equilibrate to room temperature for three hours. The reaction was quenched with dH2O, washed with 2 x 20 mL aliquots of brine. The aqueous phase was extracted with CH2Cl2 (2 x 10 mL), and the combined organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure. Column chromatography with a 2.5:1 ratio of hexanes:ethyl acetate afforded the below compounds. [Note: Bis(p-nitrobenzyloxy) disulfide, bis(4-methoxybenzyloxy) disulfide, bis(4-tertbutylbenzyloxy) disulfide, and bis(4-benzyloxy) disulfide have been previously synthesized in another laboratory with reported spectra in Ref. [13]. With the exception of bis(4-benzyloxy) disulfide, all spectra reported was almost identical to those reported below. For bis(4-benzyloxy) disulfide, Ref. [13] incorrectly assigned the aromatic signals as d 7.39 (m, 15H) instead of our d 7.17 (m, 10H). In addition, bis(p-nitrobenzyloxy) disulfide, bis(4-methoxybenzyloxy) disulfide, bis(4-methylbenzyloxy) disulfide, bis(4-benzyloxy) disulfide, and bis(4-chlorobenzyloxy) disulfide were also reported in Ref. [4]. The mp. and NMR matched our samples. Bis(4-phenylbenzyloxy) disulfide was first synthesized and fully characterized in our laboratory in Ref. [16]. Bis(4-phenoxybenzyloxy) disulfide, bis(4-cyanobenzyloxy) disulfide, and bis(4-cyanobenzyloxy) disulfide all were previously synthesized and fully characterized from our laboratory and reportedin Ref. [18].

The synthetic route of 873-76-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stoutenburg, Eric G.; Gryn’Ova, Ganna; Coote, Michelle L.; Priefer, Ronny; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 136; PC; (2015); p. 1924 – 1931;,
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Reference of 37585-25-4, 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 37585-25-4, name is (2-Amino-5-chlorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Oxidation of (2-amino-phenyl)-methanols (3) to 2-amino-benzaldehydes (4) -General procedure; [0082] (2-Amino-phenyl)-methanol (12 mmol) in dry diethyl ether (25 ml_) is added dropwise to a mixture of manganese dioxide (48 mmol) in dry diethyl ether (25 ml_) and the mixture is stirred at rt overnight. The solution is filtered through a celite and the solvent is removed at reduced pressure. The crude product is used in the next step without further purification.; 2-Amino-5-crtloro-benzaldehyde; Yield 99%; 1H NMR (CDCI3): 6.14 (br s, 2H); 6.61 (d, 9 Hz, 1 H); 7.25 (dd, 9 and 2 Hz, 1 H); 7.44 (d, 2 Hz, 1 H) and 9.80 (s, 1 H).

According to the analysis of related databases, 37585-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERZ PHARMA GMBH & CO KGAA; HENRICH, Markus; BAUER, Angela; NAGAL, Jens; SLADEK, Meik; PARSONS, Christopher, Graham, Raphael; DANYSZ, Wojciech; KRAUSS, Valerjans; ROZHKOVS, Jevgenijs; STARCHENKOVS, Igors; TRIFANOVA, Dina; WO2010/37533; (2010); A1;,
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Related Products of 100-86-7, 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.100-86-7, name is 2-Methyl-1-phenyl-2-propanol, molecular formula is C10H14O, molecular weight is 150.22, as common compound, the synthetic route is as follows.

50mL egg-shaped flask was added N – saccharin trifluoromethylthio group 1 (110mg, 0.39mmol), 2- methyl-3-phenyl propanol (45.0mg, 0.3mmol), 96muL triethylamine (0.69mmol), in dichloromethane (5 mL), at room temperature for 5min.After completion of the reaction, the reaction solution rapidly by about 6 millimeters silica gel column, the column with the amount of methylene chloride and washed twice, and the combined organic liquid, spin dry to give trifluoromethyl – (2-benzyl) isopropyl thio peroxide (62mg, 83% isolated yield).Purity by NMR identified more than 95%.Trifluoromethyl – (2-benzyl-yl) thio-isopropyl peroxy (((2-Methyl-1-phenylpropan-2-YL) Oxy) (trifluoromethyl) sulfane):

Statistics shows that 100-86-7 is playing an increasingly important role. we look forward to future research findings about 2-Methyl-1-phenyl-2-propanol.

Reference:
Patent; Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences; Chen, Qilong; Xu, Chunfa; (25 pag.)CN104945298; (2016); B;,
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Adding a certain compound to certain chemical reactions, such as: 42042-68-2, 4-(Methylamino)butan-1-ol, 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, Recommanded Product: 4-(Methylamino)butan-1-ol, blongs to alcohols-buliding-blocks compound. Recommanded Product: 4-(Methylamino)butan-1-ol

To a solution of 3.00 g of 2-chloro-5,6-di-p-tolylpyrazine and 1.57 g of 4-(methylamino)-1-butanol in 15 ml of N,N-dimethylformamide, 2.26 g of potassium carbonate was added.. After heating with stirring at 100C for 26 hours, the reaction solution was extracted with diethyl ether after adding ice water.. The extract was washed in turn with water and saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure.. The residue was purified by silica gel column chromatography and the resulting crystal was washed with diisopropyl ether to obtain 2.76 g of the desired compound as a colorless crystal having a melting point of 94 to 96C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,42042-68-2, 4-(Methylamino)butan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; EP1400518; (2004); A1;,
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Reference of 7397-62-8, 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 7397-62-8 as follows.

Example 36 Butyl 3-amino-6-benzyl-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine-2-carboxylate A solution of 1.0 gm (0.008 mol) of butyl glycolate in 8 ml of absolute dioxane was added dropwise to a suspension of 0.4 gm (0.008 mol) of 50% sodium hydride in 5 ml of absolute dioxane, and the mixture was stirred for one hour at room temperature. Then, while the mixture was cooled with ice, a solution of 1.0 gm (0.004 mol) of 1-benzyl-4-chloro-5-cyano-2,3,6,7-tetrahydro-1H-azepine in 15 ml of absolute dioxane was added, and the mixture was stirred for one hour. The reaction mixture was then poured into about 80 ml of ice-cold water, and the aqueous mixture was extracted three times with ethyl acetate. The combined organic phases were washed twice with water, dried over sodium sulfate and concentrated by evaporation. The residue was purified by column chromatography on silicagel, using toluene/ethyl acetate (7:3) as eluant. Yield: 0.2 gm (14% of theory). Melting point: <20 C. Calc.: molecular peak m/e=342. Found: molecular peak m/e=342. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7397-62-8, its application will become more common. Reference:
Patent; Dr. Karl Thomae Gesellschaft mit beschrankter Haftung; US4414225; (1983); A;,
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Reference of 2425-41-4, 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. 2425-41-4, name is (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol, molecular formula is C12H16O4, The 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.

To a solution of 5109 (1 0.0 g, 44.6 mmol) in dichloromethane (180 ml) under argon were addedbromoacetonitrile (13.0 g, 108.4 mmol), Silver( I) oxide (20.7 g, 89.2 mmol), and tetrabutylammonium iodide (3.3 g, 8.92 mmol), and the resulting mixture was stirred overnight. The mixture was filtered overCelite, and the filtrate was evaporated to give a black residue, which was subjected to flash silica gelcolumn purification on ISCO companion (hexane/ethyl acetate, 15 – 90%) to give 5.55 g (41 %) of thedesired compound S127 as a viscous oil. ESI MS for C15H1sN204 calculated 302.3, observed [M+H]+ 303.3.

According to the analysis of related databases, 2425-41-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLSTICE BIOLOGICS, LTD.; SAKAMURI, Sukumar; BRADSHAW, Curt, W.; ELTEPU, Laxman; MEADE, Bryan, R.; LAM, Son; (237 pag.)WO2018/35380; (2018); 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. 109-83-1, name is 2-(Methylamino)ethanol. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(Methylamino)ethanol

A mixture of 4.50 g (19.17 mmol) of product from 1a, 1.69 g (21.10 mmol) of N-methylaminoethanol (BASF), 6.68 ml (47.90 mmol) of triethylamine and 150 ml dichloromethane is stirred overnight at ambient temperature. The reaction mixture is then washed with 0.5 M HCl, saturated sodium hydrogen carbonate solution, water and saturated sodium chloride solution, dried on sodium sulphate and evaporated to dryness in vacuo.C12H19NO4S (273.35)[M+H]+=274TLC: silica gel, dichloromethane/ethanol 19:1, Rf value=0.43

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, 109-83-1, 2-(Methylamino)ethanol.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/197664; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4461-39-6, N-(2-Hydroxyethyl)-1,3-propanediamine, 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, Recommanded Product: 4461-39-6, blongs to alcohols-buliding-blocks compound. Recommanded Product: 4461-39-6

General procedure: A suspension oftert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate5(1 eq.), the corresponding amine (2 eq.) and acetic acid (2 – 5 eq.) in DCE (2 ml) was stirred at RT for 30 min.To this suspension was added sodium triacetoxyborohydride (5 eq.).The resulted mixture was stirred at RT for 18 – 72 hrs.The reaction mixture was diluted with 5 ml of saturated sodium carbonate and extracted with DCM (3 x 10 ml).The combined organic layers were dried over sodium sulfate, filtered and concentratedinvacuo.The crude product was purified by Biotage flash chromatography or was used directly in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4461-39-6, N-(2-Hydroxyethyl)-1,3-propanediamine, and friends who are interested can also refer to it.

Reference:
Article; Chen, Yan; Sit, Sing-Yuen; Chen, Jie; Swidorski, Jacob J.; Liu, Zheng; Sin, Ny; Venables, Brian L.; Parker, Dawn D.; Nowicka-Sans, Beata; Lin, Zeyu; Li, Zhufang; Terry, Brian J.; Protack, Tricia; Rahematpura, Sandhya; Hanumegowda, Umesh; Jenkins, Susan; Krystal, Mark; Dicker, Ira D.; Meanwell, Nicholas A.; Regueiro-Ren, Alicia; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1550 – 1557;,
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Adding a certain compound to certain chemical reactions, such as: 35364-79-5, 2-(3,4-Dichlorophenyl)ethanol, 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, 35364-79-5, blongs to alcohols-buliding-blocks compound. Quality Control of 2-(3,4-Dichlorophenyl)ethanol

To a solution of alcohol 35 (0.5 mmol) in CH2Cl2 (10 mL) at 0 Cwas added TEA (0.55 mmol, 1.1 equiv) and methanesulfonyl chloride(0.55 mmol, 1.1 equiv). The mixture was stirred at 0 C for anadditional 2 h, and concentrated to provide crude compound 36. To a solution of 2-(3,4-dichlorophenyl)ethan-1-ol (0.5 mmol) andK2CO3 (1 mmol, 2 equiv) in DMF was added compound 36(0.5 mmol). The reaction mixture was stirred at 60 C overnight,cooled, and partitioned between H2O (50 mL) and EtOAc (30 mL).The aqueous layer was extracted twice using EtOAc (30 mL 2).The combined organic layers were washed using brine, dried overNa2SO4, and concentrated. The crude material was purified by flashchromatography to give compound 5 (28%): 1H NMR (400 MHz,CDCl3): d 7.78 (d, J 8.0 Hz, 2H), 7.60 (d, J 8.0 Hz, 2H), 7.53 (d,J 8.0 Hz, 1H), 7.48 (d, J 3.6 Hz, 2H), 7.38 (d, J 3.6 Hz, 1H), 7.20(d, J 8.4 Hz, 1H), 7.01 (d, J 3.6 Hz, 1H), 4.97 (s, 2H), 3.88 (t,J 5.6 Hz, 2H), 3.04 (t, J 5.6 Hz, 2H); 13C NMR (100 MHz, CDCl3):d 149.6, 145.0, 139.3, 133.6, 132.5, 132.2, 130.8, 130.3, 130.2, 129.0,128.8, 128.3, 118.7, 117.8, 112.7, 70.0, 62.7, 35.3; HRMS (ESI): Exactmass calcd for C20H16Cl3N2OS [MH] 437.0049, found 437.0051;HPLC analysis: retention time 5.7 min, peak area 97.6%, 80:20CH3CN/H2O.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,35364-79-5, its application will become more common.

Reference:
Article; Liang, Dongdong; Li, Linhao; Lynch, Caitlin; Mackowiak, Bryan; Hedrich, William D.; Ai, Yong; Yin, Yue; Heyward, Scott; Xia, Menghang; Wang, Hongbing; Xue, Fengtian; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 84 – 99;,
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Application of 552331-15-4, 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 552331-15-4, name is 1-(5-Bromo-2-fluorophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Step-2: Synthesis of 1-(5-bromo-2-fluorophenyl)ethan-1-one To a stirred solution of 1-(5-bromo-2-fluorophenyl)ethan-1-ol (5.3 g, 24.195 mmol, 1.0 eq) in THF (50 mL) was added Dess-martin peridionane (12.314 g, 29.034 mmol, 1.2 eq) at 0 C. The resulting mixture was stirred at rt for 15 min. The progress of reaction was monitored by LCMS. The resection mixture was quenched with saturated solution of NaHCO3 (50 mL) extracted with EtOAc (2*50 mL). The combined organic extracts were washed with water (50 mL), with brine (50 mL) dried over Na2SO4 and concentrated under reduced pressure and purified by flash chromatography [silica gel 100-200 mesh; elution 0-5% EtOAc in hexane] to afford the desired compound 1-(5-bromo-2-fluorophenyl)ethan-1-one (3.78 g, 72.00%) as yellow liquid. 1H NMR (400 MHz, CDCl3) delta 7.99 (dd, J=2.63, 6.58 Hz, 1H), 7.61 (ddd, J=2.63, 4.39, 8.77 Hz, 1H), 7.05 (dd, J=8.77, 10.09 Hz, 1H), 2.64 (d, J=4.82 Hz, 3H).

According to the analysis of related databases, 552331-15-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
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