Month: May 2021

Application of 2807-30-9 ,Some common heterocyclic compound, 2807-30-9, molecular formula is C5H12O2, 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.

(1) Weigh 100g ethylene glycol mono-n-propyl ether,0.3 g of N, N-dimethylaniline,This was added to the reaction vessel with a reflux condenser,115.97 g of thionyl chloride (content of 99.3%, sulfuryl chloride content of 0.5%) was added to a constant pressure dropping funnel,Warming up to 35 C, turning on stirring,Thionyl chloride was slowly added dropwise to the reaction vessel to release sulfur dioxide and hydrogen chloride gas during the reaction,Control thionyl chloride dropping speed,The temperature of the reaction solution was maintained at 60 ± 5 C;(2) until the thionyl chloride is added dropwise,According to the reaction gas evolution rate gradually warmed to 95 ,Until no gas release, continue to heat 1h get crude,After the crude product is cooled down to 40 C, a certain amount of lye is added and stirred,The remaining thionyl chloride decomposition and neutralization of acid,Then add a certain amount of water for hydrolysis,After standing for liquid separation, 117.65 g of 2-propoxychloroethane was obtained.After testing, the chromatographic content of the product was 99.84%Yield of 99.89%.

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. 2807-30-9, 2-Propoxyethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shandong Kaisheng New Materials Co., Ltd.; Shi Yufei; Zhang Taiming; Han Nannan; Wang Ronghai; Xue Juqiang; Wang Jun; Li Guanghui; Huang Guiqing; (5 pag.)CN106831368; (2017); A;,
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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.2566-44-1, name is 2-Cyclopropylethanol, molecular formula is C5H10O, molecular weight is 86.13, as common compound, the synthetic route is as follows.Safety of 2-Cyclopropylethanol

EXAMPLE 172; 2-[9-(2-cyclopropylethoxy)-6-(2-hydroxy-2-methylpropyl)-leta-phenanthro[9,10-d]imidazol-2-yl]-5- fluoroisophthalonitrile; Step 1; 3-bromo-6-(2-cyclopropylethoxy)phenanthrene; To a mixture of 6-bromophenanthren-3-ol (3 g, 11 mmol) from Step 1 of Route A of Example 168, 2-cyclopropylethanol (2.85 g, 33 mmol) and triphenylphosphine (5.78 g, 22 mmol) in THF (50 mL) was added di-tert-butylazodicarboxylate (5.08 g, 22 mmol). The reaction mixture was stirred at room temperature overnight, then quenched with water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The material was purified by flash chromatography on silica (100% hexanes) to afford 3- bromo-6-(2-cyclopropylethoxy)phenanthrene.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2566-44-1, 2-Cyclopropylethanol, and friends who are interested can also refer to it.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2007/59610; (2007); A1;,
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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 116-02-9, name is 3,3,5-Trimethylcyclohexanol. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C9H18O

a) 426g (3,00 Mol) of Homomenthol is added to the above-mentioned filtrate, the temperature is raised to 60C and under stirring and a vacuum of lOOmbar the Ethyl acetate is distilled off the reaction mixture. Then 56g of Sulfuric acid are added at a tempera- ture of 50C within 20minutes, stirring is continued for 6h. For work-up 500g of Toluene are added to the reaction mixture and after cooling to 5-10C the dosage of 500g of iced water follows. After separation of the water layer the organic layer is washed to neutral with aqueous Sodium hydroxide solution (10% w/w) and finally with saturated aqueous Sodium chloride solution. After separation of the water layer the organic layer is distilled resulting 250g (0,93 Mol) of product. Yield (overall): 58% of theory.

With the rapid development of chemical substances, we look forward to future research findings about 116-02-9.

Reference:
Patent; SYMRISE AG; STUHLMANN, Dominik; MEYER, Imke; KOCH, Oskar; OERTLING, Helko; HERRMANN, Martina; GOeMANN, Claudia; WO2014/198602; (2014); 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. 117284-59-0, name is 2-(2,2-Difluorocyclopropyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-(2,2-Difluorocyclopropyl)ethanol

5.41 g (54.1 mmol) of chromium trioxide was dissolved in 90.2 mL of 1.5 M sulfuric acid solution, and cooled at with stirring 0 C. 3.3g (27.1 mmol) of 2-(2,2-difluorocyclopropyl)ethanol was dissolved in 90.2 mL of acetone. The mixture was added dropwise to a chromium trioxide-sulfuric acid solution with stirring at 0 C. After the addition was completed, the reaction solution was stirred at 0 C for 4 hours. The organic layer was extracted with diethyl ether (50 mL34). The combined organic layers were washed with brine. It was then extracted with 2M sodium hydroxide solution (50 mL34) and the aqueous layers were combined. The aqueous layer was acidified to pH < 1 with sulfuric acid with stirring in an ice bath. The organic layer was extracted with diethyl ether (50 mL 3 4), and the combined organic layers were washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated to give 3.4g colorless liquid 2-(2,2-difluorocyclopropyl)acetic acid in 92% yield. 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, 117284-59-0, 2-(2,2-Difluorocyclopropyl)ethanol. Reference:
Patent; Shanghai Institute Of Materia Medica Chinese Academy of Sciences; LIU, Hong; ZHOU, Yu; XIA, Wenjing; ZHANG, Dong; JIANG, Hualiang; CHEN, Kaixian; (49 pag.)EP3459948; (2019); A1;,
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Synthetic Route of 52244-70-9, 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. 52244-70-9, name is 4-(4-Methoxyphenyl)-1-butanol. A new synthetic method of this compound is introduced below.

To a stirred solution of 4-(4-methoxyphenyl)butanol (1 equiv.) in dry dichloromethane at -10°C under an argon atmosphere was added boron tribromide (2.7 equiv., using a 1 M solution of boron tribromide in CH2Cl2). Stirring was continued at that temperature until completion of the reaction (4 hours). Unreacted boron tribromide was destroyed by addition of aqueous saturated NaHCO3 solution at 0°C. The resulting mixture diluted with CH2Cl? and water, the organic phase was separated, washed with brine, dried (MgSO4), and evaporated. Purification by flash column chromatography on silica gel (30percent diethyl ether-hexane) afforded the title compound in 42percent yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52244-70-9, its application will become more common.

Reference:
Patent; NORTHEASTERN UNIVERSITY; WO2009/52319; (2009); A1;,
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Application of 506-43-4, Adding some certain compound to certain chemical reactions, such as: 506-43-4, name is (9Z,12Z)-Octadeca-9,12-dien-1-ol,molecular formula is C18H34O, 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 506-43-4.

Synthesis of linoleyl mesylate or (9Z,12Z)-octadeca-9,12-dienyl methanesulfonate (2) Referring to Scheme 10, triethylamine (13.13 g, 130 mmol) was added to a solution of the linoleyl alcohol 1 (26.6 g, 100 mmol) in dichloromethane (100 mL) and the solution was cooled in an ice-bath. To this cold solution, a solution of methanesulfonyl chloride (12.6 g, 110 mmol) in dichloromethane (60 mL) was added dropwise; after the completion of the addition, the reaction mixture was allowed to warm to ambient temperature and stirred overnight. Completion of the reaction was confirmed by TLC. The reaction mixture was diluted with dichloromethane (200 mL), washed with water (200 mL), satd. NaHCO3 (200 mL), brine (100 mL) and dried over anhydrous Na2SO4. After evaporation of solvent in vacuo the crude product was purified by flash silica column chromatography using 0-10% Et2O in hexane. The pure fractions were combined and concentrated to obtain the mesylate 2 as colorless oil (30.6 g, 89%). 1H NMR (400 MHz, CDCl3): delta=5.42-5.21 (m, 4H), 4.20 (t, 2H), 3.06 (s, 3H), 2.79 (t, 2H), 2.19-2.00 (m, 4H), 1.90-1.70 (m, 2H), 1.06-1.18 (m, 18H), 0.88 (t, 3H). 13C NMR (CDCl3): delta=130.76, 130.54, 128.6, 128.4, 70.67, 37.9, 32.05, 30.12, 29.87, 29.85, 29.68, 29.65, 29.53, 27.72, 27.71, 26.15, 25.94, 23.09, 14.60. MS. MW calc. for C19H36O3S: 344.53. found: 343.52 [M-H].

According to the analysis of related databases, 506-43-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Arbutus Biopharma Corporation; Manoharan, Muthiah; Rajeev, Kallanthottathil G.; Jayaraman, Muthusamy; Butler, David; Kapoor, Mamta; Kainthan, Rajesh Kumar; (106 pag.)US9687550; (2017); B2;,
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Related Products of 5259-98-3, 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 5259-98-3 as follows.

4-chlorobutan-1-ol (1.0 equiv, 46.05 mmol, 5.00 g) and sodium azide (2.0 equiv, 92.10mmol, 5.99g) were dissolved in Water (50 mL) and refluxed at 100°C overnight. Reaction progression was checked by TLC, which showed full conversion. The reaction was left to cool to room temperature and the product was extracted with diethylether (5x). The combined organic layers were washed with brine and dried with sodium sulfate. Concentration in vacuo yielded the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5259-98-3, its application will become more common.

Reference:
Article; Saarbach, Jacques; Masi, Daniela; Zambaldo, Claudio; Winssinger, Nicolas; Bioorganic and Medicinal Chemistry; vol. 25; 19; (2017); p. 5171 – 5177;,
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Synthetic Route of 111-45-5, 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 111-45-5, name is 2-(Allyloxy)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of alcohol 4A (5.1 g, 1.0 eq) in DCM (50 mL) cooled to 0 C was added a solution of Et3N (7 g, 1.4 eq) followed by dropwise addition of MsCl (6.9 g, 1.2 eq). The reaction was stirred at 0 C for 2 hrs. The reaction mixture was quenched with water and the organic layer was washed with NaHC03 (10 mL) and brine, dried over Na2S04. The crude mixture was filtered and evaporated under reduced pressure to afford the compound 4B, which was used for next step reaction without further purification.

According to the analysis of related databases, 111-45-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; MA, Jingyuan; EMAYAN, Kumaraswamy; ADLER, Marc; (327 pag.)WO2018/9417; (2018); A1;,
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Electric Literature of 34598-50-0, 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. 34598-50-0, name is 5-Bromo-2,3-dihydro-1H-inden-1-ol. A new synthetic method of this compound is introduced below.

Step B: [(5-bromo-2,3-dihvdro-lH-inden-yl’)oxy]ft-butyl)dimethylsilane 5-bromoindan-l-ol (260 mg, 1.22 mmol) obtained in Step A was dissolved in methylene chloride (50 mL) and the mixture was cooled to 00C, followed by addition of trimethyldimethylsilyl trifluoromeihane sulfonate (355 mg, 1.34 mmol). After stirring for 30 min, the reaction temperature was elevated to room temperature. The reaction was terminated with addition of a saturated aqueous solution of ammonium chloride, followed by extraction with a 0.5N HCl aqueous solution. The organic layer was taken, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was directly used in subsequent reactions without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,34598-50-0, 5-Bromo-2,3-dihydro-1H-inden-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; LG LIFE SCIENCES, LTD.; WO2009/38411; (2009); A2;,
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Synthetic Route of 17100-58-2, 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. 17100-58-2, name is (4-Bromo-2-methylphenyl)methanol, molecular formula is C8H9BrO, 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 ID (9.30 g, 46.3 mmol) in CH2CI2 (200 mL) under argon was added oxalyl chloride (10.1 mL, 116 mmol) at -78 C; then DMSO (9.85 mL, 139 mmol) was added dropwise with a venting needle. After the addition was complete, the venting needle was removed and the reaction mixture was stirred at -78 C under argon for 30 min. Then, NEt3 (38.7 mL, 278 mmol) was added dropwise. After stirring at the same temperature for 3 h, the reaction mixture was diluted with water (20 mL) and CH2C12 (50 mL) and the layers were separated. The aqueous layer was further extracted with CH2CI2 (3 x 100 mL) and the combined organic extracts were washed with water and brine, dried over MgS04, filtered, and concentrated. The crude product was purified by silica chromatography to give IE (yellow oil, 6.70 g, 33.7 mmol, 73% yield). 1H NMR (400 MHz, CDC13) delta 10.22 (1 H, s), 7.66 (1 H, d, J=8.28 Hz), 7.51 (1 H, dd, J=8.28, 1.76 Hz), 7.45 (1 H, s), 2.65 (3 H, s).

According to the analysis of related databases, 17100-58-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; ELLSWORTH, Bruce A; JURICA, Elizabeth A; WO2015/171757; (2015); A1;,
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