Category: alcohols-buliding-blocks

Synthetic Route of 702-82-9 ,Some common heterocyclic compound, 702-82-9, molecular formula is C10H17NO, 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: To a suspension of 3a (206 mg, 0.748 mmol) in DMF (10 mL) was added DIPEA (0.392 mL, 2.245 mmol) and the solution was stirred at rt for 30 min. HBTU (568 mg, 1.497 mmol) was added portion wise, followed by the addition of 1-aminoadamantane (0.136 g, 0.898 mmol). The mixture was stirred at rt for 4 h and diluted with EtOAc (60 mL), washed with water (3 x 10 mL), HCl (0.5 M, 10 mL), water (10 mL) and brine (15 mL). Solvents were removed under reduced pressure and the residue was purified with flash chromatography using hexane:EtOAc (10:1 to 2:1) to give RS-005 (263 mg, 0.644 mmol, 86% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,702-82-9, its application will become more common.

Reference:
Article; Slavik, Roger; Herde, Adrienne Mueller; Bieri, Daniel; Weber, Markus; Schibli, Roger; Kraemer, Stefanie D.; Ametamey, Simon M.; Mu, Linjing; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 554 – 564;,
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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. 311-86-4, name is 2-Bromo-3,3,3-trifluoropropan-1-ol, molecular formula is C3H4BrF3O, 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. Recommanded Product: 2-Bromo-3,3,3-trifluoropropan-1-ol

2-bromo-1 ,1 , 1-trifluoropropan-3-ol (10 g, 0.0524mol) was placed in a 2-necked round bottom flask fitted with a distillation set up and then heated to 95 C. Sodium hydroxide (3 g, 0.0754 mol) was dissolved in water (12 g) at 0 C with stirring. Once the solution was homogenous it was then added dropwise to the 2-bromo-1 ,1 , 1-trifluoropropan-3-ol with rapid stirring via dropping funnel. As the head temperature reached 60 C clear liquid was collected in a receiver flask (4.2 g). GC area%: 1 , 1 , 1-trifluoro-1 ,2- epoxypropane (52%), 2-bromo-3,3,3-trifluoropropene + ethyl ether (26%), 3-acetoxy-2- bromo-1 , 1 , 1-trifluoropropane (7%), acetone (2%), unknown (13%).

With the rapid development of chemical substances, we look forward to future research findings about 311-86-4.

Reference:
Patent; MEXICHEM FLUOR S.A. DE C.V.; MURRAY, James Henry; SHARRATT, Andrew Paul; (32 pag.)WO2018/197897; (2018); A1;,
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Application of 3840-31-1, Adding some certain compound to certain chemical reactions, such as: 3840-31-1, name is (3,4,5-Trimethoxyphenyl)methanol,molecular formula is C10H14O4, 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 3840-31-1.

Commercial available (3,4,5-trimethoxyphenyl)methanol (25 g, 126 mmol) was dissolved in THF (150 mL). Sodium hydride (3.93 g, 164 mmol) was added portionwise at 0C. The reaction mixture was stirred at 0C for 10 min. Then iodomethane (10.21 ml, 164 mmol) was added drop wise. The resultant mixture was stirred from 0C to rt for 3 hours and quenched by pouring into ice. The mixture was extracted with ethyl acetate, washed by brine and dried by anhydrous sodium sulfate. After filtered and concentrated, the afforded residue was purified by silica gel column. Colorless oil l,2,3-trimethoxy-5-(methoxymethyl)benzene (26.44 g, 125 mmol, 99 % yield) was afforded. 1H NMR (400 MHz, CDC13) delta 6.53 (s, 2H), 4.35 (s, 2H), 3.82 (s, 6H), 3.79 (s, 3H), 3.36 (s, 3H). 13C NMR (101 MHz, CDC13) delta 153.22 (2C), 137.36, 133.82, 104.53 (2C), 74.83, 60.76, 58.11, 56.02 (2C). ESI-MS m/z: 235.0 (MNa+).

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. 3840-31-1, (3,4,5-Trimethoxyphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNITED STATES OF AMERICA, represented by THE SECRETARY, DEPARTMENT OF HEALTH & HUMAN SERVICES; ZHAO, Xue, Zhi; HUGHES, Stephen, H.; VU, Bao-Han, Christie; SMITH, Steven; JOHNSON, Barry; POMMIER, Yves; BURKE, Terrence, R., Jr.; WO2013/16441; (2013); 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.7735-42-4, name is 1,16-Hexadecanediol, molecular formula is C16H34O2, molecular weight is 258.44, as common compound, the synthetic route is as follows.category: alcohols-buliding-blocks

The diol 14 (1 .047 g, 4.05 mmol) was dissolved in cyclohexane (30 mL) and vigorously stirred with 48% HBr (0.5 mL, 4.46 mmol, 1.1 eq.). The mixture was refluxed for 6 h, diluted with water (50 mL) and the phases were separated. The aqueous phase was extracted with a mixture of dichloromethane and methanol (v/v, 4:1 3 x 20 mL). The combined organic layer was dried over MgS04. The product was purified by column chromatography with silica gel (6 x 6 cm, cyclohexane/ethyl acetate, 8:1 ) and isolated as a white solid. Yield: 4.598 g (96%). Traces of 1 ,16-dibromohexadecane were also found. 15 M.p.: 65 C (lit. 53-54 C) 1H-NMR (300 MHz, CDCI3) delta [ppm]: 1.26-1.47 (m, 23 H, 4-CH2 to 14-CH2, 1 -OH), 1.51 -1.62 (m, 4 H, 2-CH2, 3-CH2), 1 .85 (m, 2 H, 15-CH2), 3.41 (t, 3JH,H = 6.9 Hz, 2 H, 16-CH2), 3.64 (t, 3JH,H = 6.6 HZ, 2 H, 1 -CH2). 13C-NMR (75 MHz, CDCI3) delta [ppm]: 25.9 (t, C-3), 28.3, 28.9, 29.6, 29.7, 29.8 (t, C-4 to C-14), 33.0 (t, C-2, C-15), 34.3 (t, C-16), 63.3 (t, C-1 ). Refs.: M.p. P. Chuit, J. Hausser, Helv. Chim. Acta 1929, 72,850-859. 1H-NMR spectroscopic data agree with those given by: S. Takanashi, M. Takagi, H. Takikawa; K. Mori, J. Chem. Soc, Perkin Trans. 1 1998, 1603-1606.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7735-42-4, 1,16-Hexadecanediol, and friends who are interested can also refer to it.

Reference:
Patent; WESTFAELISCHE WILHELMS-UNIVERSITAET MUENSTER; HAUFE, Guenter; LEVKAU, Bodo; SCHAEFERS, Michael; SCHILSON, Stefani Silke; KEUL, Petra; WO2013/26765; (2013); A1;,
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Electric Literature of 10029-04-6, Adding some certain compound to certain chemical reactions, such as: 10029-04-6, name is Ethyl 2-(hydroxymethyl)acrylate,molecular formula is C6H10O3, 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 10029-04-6.

Example 1(0189)With reference to FIG. 1, the first generic compound in the synthetic sequence (structure I) is prepared where X is CN, W is H, X? is CO2Et, and L is H.(0190)More specifically, in a 1 liter three-necked flask, alpha(hydroxymethyl)ethylacrylate (260.0 g, 2.0 mol) and 1.1 equivalent of cyanoacetic acid (187.0 g, 2.2 mol) were suspended in toluene (420 mL) with hydroquinone (0.8 g). The mixture was heated at a temperature of 90 C. until the cyanoacetic acid melted, at which point a catalytic amount (two drops) of sulfuric acid was added. The reaction mixture was stirred with heating at a temperature of 125 C. with a Dean-Stark apparatus attached to remove the water.(0191)The reaction mixture was washed with dilute aqueous sodium bicarbonate to remove excess cyanoacetic acid, then with dilute hydrochloric acid and finally with brine. The solvent (toluene) was removed under reduced pressure and the residue with an added 1 g of hydroquinone was distilled (b.p. 130 C. at 0.2 mm Hg) to furnish 197 g of the final product in a yield of 51%. Spectral confirmation is given below.(0192)1H-NMR (60 MHz, CDCl3): delta=1.32 (t, 3H), 3.49 (s, 2H), 4.24 (q, 2H), 4.92 (s, 2H), 5.90 (s, 1H), 6.41 (s, 1H) ppm.(0193)FT-IR (film): 2983.1, 2929.4, 2259.3, 1750.8, 1712.7, 1638.8, 1447.4, 1395.9, 1367.9, 1336.0, 1309.1, 1270.0, 1176.4, 1152.9, 1023.5, 957.7, 879.3, 859.1, 815.9 cm-1.

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. 10029-04-6, Ethyl 2-(hydroxymethyl)acrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Henkel Ireland Limited; Gherardi, Stefano; McArdle, Ciaran B.; Faimani, Giovanni; Loschen, Christoph; US8399698; (2013); B1;,
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Electric Literature of 52059-53-7, 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. 52059-53-7, name is 2-(3-Fluorophenyl)ethanol. A new synthetic method of this compound is introduced below.

A mixture of 2-(3-fluorophenyl)ethan-1-ol (0.031 g, 0.223 mmol, 5 equiv), 60%NaH (8.90 mg, 0.223 mmol, 5 equiv), and isopropyl (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin- 1 -yl)-6?-fluoro-6-methyl- [3,3 ?-bipyridinj -5-yl)acetate (0.021 g, 0.045 mmol, 1 equiv) in THF (1.5 mL) was stirred at ambient temperature for 1 h. Upon complete addition, 5 M NaOH (0.089 mL, 0.445 mmol, 10 equiv) was added and the mixture was heated at 80 C for 2 h. The reaction was allowed to cool to ambienttemperature, filtered, and purified by preparative reverse phase HPLC to provide the product (10 mg, 40%). ?H NMR (500 MHz, DMSO-d6) 8.18 – 7.97 (m, 2H), 7.73 – 7.60 (m, 1H), 7.40 – 7.29 (m, 1H), 7.21 – 6.94 (m, 3H), 6.93 – 6.83 (m, 1H), 5.86 – 5.75 (m, 1H), 4.62 -4.50 (m, 2H), 3.14 -3.02 (m, 1H), 1.38 – 1.24 (m, 3H), 1.18 – 1.02 (m, 1OH),0.91 – 0.70 (m, 6H). LCMS (M+1): 550.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52059-53-7, 2-(3-Fluorophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 83647-43-2, (3-Bromo-2-methylphenyl)methanol, 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, Product Details of 83647-43-2, blongs to alcohols-buliding-blocks compound. Product Details of 83647-43-2

To a solution of 20.00 g (99.47 mmol, 1.0 eq) of (3-bromo-2-methyl-phenyl)methanol 1A and 24.26 g (198.94 mmol, 2.0 eq) of phenylboronic acid in 156 mL of toluene and 52mL of EtOH, were added 812.3 mg (0.995 mmol, 0.01 eq) of Pd(dppf)Cl2.CH2Cl2 and 25.07g (2 M, 149.21 mL, 3.0 eq) of NaHCC under nitrogen gas. The mixture was stirred at 80C for 12 hours. The mixture was separated, and the aqueous phase was extracted with 2 x 400 mL of ethyl acetate (EtOAc). The combined organic phase was washed with 2 x 200 mL of brine, dried over Na2SC>4, filtered and the solvent was concentrated. The residue was purified by column eluted with petroleum ether/ethyl acetate = 25/1-10/1 to give crude product (25 g) as a yellow solid. The solid was smashed in 100 mL of petroleum ether, and the suspension was filtered to give 15.00 g (74.62%) of (2-methyl-[l,l’-biphenyl]-3-yl)methanol as a white solid. lH NMR (400 MHz, CDC13): delta 7.40-7.31 (m, 4H) 7.25-7.22 (m, 3H) 4.75-4.74 (m, 2H) 2.21 (m, 3H) 1.62~1.59(m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,83647-43-2, (3-Bromo-2-methylphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; ARBUTUS BIOPHARMA CORPORATION; BI, Yingzhi; DORSEY, Bruce D.; MOORE, Christopher Brooks; (75 pag.)WO2018/200571; (2018); A1;,
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Electric Literature of 756520-66-8 ,Some common heterocyclic compound, 756520-66-8, molecular formula is C8H7Cl2FO, 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 triphenyl phosphine (8. 2 G, 0. 03 mol) and DEAD (13. 65 mL of a 40% solution in toluene) in THF (200 mL) at 0 C was added a solution of 1- (2, 6-DICHLORO-3-FLUORO-PHENYL)- ethanol (4. 55 G, 0. 021 mol) and 3-hydroxy-nitropyridine (3. 35 G, 0. 023 mol) in THF (200 mL). The resulting bright orange solution was stirred under a nitrogen atmosphere at ambient temperature for 4 hours at which point all starting materials had been consumed. The solvent was removed, and the crude material was dry loaded onto silica gel, and eluted with ethyl acetate-hexanes (20 : 80) to yield 3- (2, 6-DICHLORO-3-FLUORO-BENZYLOXY)-2-NITRO-PYRIDINE (6. 21 G, 0. 021 mol, 98%) as a pink SOLID. 1H NMR (CDCl3, 300 MHz) 1. 8-1. 85 (d, 3H), 6. 0-6. 15 (q, 1H), 7. 0-7. 1 (t, 1H), 7. 2-7. 21 (d, 1H), 7. 25-7. 5 (m, 2H), 8. 0-8. 05 (d, 1 H).

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. 756520-66-8, 1-(2,6-Dichloro-3-fluorophenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUGEN, INC.; WO2004/76412; (2004); A2;,
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Electric Literature of 33420-52-9, 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 33420-52-9, name is 2,2-Difluoropropan-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

Trifluoromethanesulfonic anhydride (3.29 ml, 19.5 mmol) was added dropwise to a solution of 2,2-difluoropropan-1-ol (1.7 g, 18 mmol) in DCM (40 mL) at -10 C. (salt/ice bath). 2,6-Dimethylpyridine (2.5 mL, 21 mmol) was then added, and the reaction was stirred for 1 hour under these conditions. The reaction was then washed with water (*2), and the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure (vacuum ?200 mbars) to afford 2,2-difluoropropyl trifluoromethanesulfonate (2.1 g, 52%) as a red oil. 1H NMR (400 MHz, CHLOROFORM-d, 27 C.) 4.48 (2H, t), 1.73 (3H, t).

According to the analysis of related databases, 33420-52-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; BARLAAM, Bernard Christophe; O’DONOVAN, Daniel Hillebrand; HUGHES, Samantha Jayne; MOSS, Thomas Andrew; NISSINK, Johannes Wilhelmus Maria; SCOTT, James Stewart; YANG, Bin; (148 pag.)US2018/111931; (2018); A1;,
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Electric Literature of 627-18-9, 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 627-18-9, name is 3-Bromopropan-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 3,4-Dihydropyran (DHP, 15 mmol) was added slowly to a stirred solution of bromohydrin (10 mmol) and p-toluenesulfonic acid (1 mmol) in dichloromethane (20 mL) on ice bath. After stirring at room temperature overnight, the reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography to afford 1-5 as a light yellow oil. 2-(3-Bromopropoxy)tetrahydro-2H-pyran (1). Yield 94.2%. 1H NMR spectrum, delta, ppm: 1.37-1.55 m (4H), 1.57-1.65 m (1H), 1.70-1.78 m (1H), 2.01-2.10 m (2H), 3.37-3.49 m (4H), 3.73-3.83 m (2H), 4.49-4.55 m (1H). 13C NMR spectrum, deltaC, ppm: 19.4, 25.4, 30.5, 30.6, 32.8, 62.1, 64.8, 98.7.

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 627-18-9, 3-Bromopropan-1-ol.

Reference:
Article; Zhang; Dong; Meng; Huang; Li; Russian Journal of General Chemistry; vol. 88; 11; (2018); p. 2388 – 2393; Zh. Obshch. Khim.;,
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