Month: June 2021

Reference of 27489-62-9, 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.27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, molecular weight is 115.1735, as common compound, the synthetic route is as follows.

A solution of trans-4-aminocyclohexanol (5 g,33 mmol) in 1,4-dioxane (100 mL) was cooled to 0 C. After 15 min, sodium hydroxide (1.6 g,40 mmol) dissolved in water (40 mL) was added and allowed to cool for an additional 15 min. Asolution of di-tert-butyl dicarbonate (7.9 g, 36 mmol) dissolved in 1,4-dioxane (65 mL) was thenadded to the solution of aminoalcohol and allowed to stir at rt for 14 h. The reaction wasquenched by the addition of 1 M HCl (100 mL) followed by EtOAc (150 mL). The layers wereseparated and the aqueous layer was extracted further with EtOAc (2 × 150 mL). The combinedorganic layers were washed sequentially with water (100 mL), brine (100 mL), and dried(Na2SO4) before being concentrated in vacuo to give a white solid (5.3 g, 75%). Note: Theproduct can be carried forward to the mesylation step without further purification

The chemical industry reduces the impact on the environment during synthesis 27489-62-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Harty, Matthew; Nagar, Mitesh; Atkinson, Logan; Legay, Christina M.; Derksen, Darren J.; Bearne, Stephen L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 390 – 393;,
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Adding a certain compound to certain chemical reactions, such as: 7589-27-7, 2-(4-Fluorophenyl)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, 7589-27-7, blongs to alcohols-buliding-blocks compound. Application In Synthesis of 2-(4-Fluorophenyl)ethanol

To a stirred solution of 4-bromophenol (81.7 g, 472 mmol), 2-(4-fluorophenyl)ethanol (79 g, 567 mmol) and Ph3P (149 g, 567 mmol) in THF (100 mL) cooled in an ice-water bath was added drop wise DEAD (93 ml, 590 mmol) over 20 min. Note: The reaction is exothermic and efficient cooling is highly recommended before initiating large scale reaction. After 1 h, cold bath was removed and stirred overnight (17 h) at rt. Then, the reaction mixture was concentrated, the resulting residue triturated with hexanes, filtered and the filter cake washed with 10percent ether/hexanes (2-lit). The filtrate was concentrated and purified by flash chromatography (silica gel column 3 ” x 11 ” ) using 4-lit hexanes and 2-lit 2percent EtO Ac/Hex to afford 1 – bromo-4-(4-fluorophenethoxy)benzene (142 g, 469 mmol, 99 percent yield) as colorless liquid (contaminated with -2.5percent Ph3P by 1HNMR). 1H NMR (500MHz, CDC13) delta 7.41 – 7.36 (m, 2H), 7.28 – 7.22 (m, 2H), 7.05 – 6.99 (m, 2H), 6.82 – 6.76 (m, 2H), 4.14 (t, J=6.9 Hz, 2H), 3.08 (t, J=6.9 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7589-27-7, its application will become more common.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; KADOW, John F.; NAIDU, B. Narasimhulu; ROMINE, Jeffrey Lee; SIVAPRAKASAM, Prasanna; ST. LAURENT, Denis R.; (204 pag.)WO2017/25864; (2017); A1;,
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Electric Literature of 4464-18-0 ,Some common heterocyclic compound, 4464-18-0, molecular formula is C9H12O3, 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.

Preparation 2 1,3,5-Tris(bromomethyl)benzene A solution of thionyl bromide (3.1 mL, 8.3 g, 0.04 M) in chloroform (25 mL) is added dropwise over a period of 10 minutes to a stirred slurry of 1,3,5-tris(hydroxymethyl)-benzene (Preparation 1, 1.9 g, 0.012 M) in chloroform (100 mL). The mixture is stirred at room temperature for four hours during which the solids dissolve into solution. The solution is heated at reflux temperature for 45 minutes, cooled to room temperature, and examined by TLC which shows the reaction is complete. The chloroform and excess thionyl bromide are removed under reduced pressure, leaving a reddish-yellow solid residue. The crude product is chromatographed on a filtration column of gravity silica gel (63-200 mmu, 60 g) in methylene chloride. The column is eluted with methylene chloride and three fractions of 250 mL each are collected. The desired product is eluted in fraction 2 (4.13 g) and is recrystallized from hexane, giving the title compound (3.20 g) as colorless crystals, mp 95.5-97.5 C. W. Reppe and W. J. Schweckendiek, Justus Liebigs Ann. Chem., 560:1041 (1948) report amp of 94 C.

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. 4464-18-0, Benzene-1,3,5-triyltrimethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Upjohn Company; US5500417; (1996); A;,
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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. 109-83-1, name is 2-(Methylamino)ethanol, the common compound, a new synthetic route is introduced below. Quality Control of 2-(Methylamino)ethanol

15.1 A solution of 20.0 g (266.3 mmol) of 2-(methylamino)ethanol was dissolved in 100 mL of CH2Cl2 and treated first with 74.23 mL (532.54 mmol, 2 eq) of Et3N then with 33.8 mL (239.64 mmol, 0.9 eq) of benzylchloroformate within a period of 1.5 h at RT. The reaction was partitioned between Et2O (*3)/aqueous 10% KHSO4 (*2), dried over Na2SO4 and evaporated to yield 37.93 g (68%) of (2-hydroxy-ethyl)-methyl-carbamic acid benzyl ester, MS: 210 (MH+).

The synthetic route of 109-83-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ackermann, Jean; Aebi, Johannes; Dehmlow, Henrietta; Hirth, Georges; Maerki, Hans-Peter; Morand, Olivier; Panday, Narendra; US2005/65210; (2005); 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. 1072-52-2, name is 2-(Aziridin-1-yl)ethanol. A new synthetic method of this compound is introduced below., Quality Control of 2-(Aziridin-1-yl)ethanol

Example 19 (Scheme 14): Preparation of 2-[(2-bromoethyl)-2-[[[2-(beta-D- gulopyranosyloxy)ethyl] amino] carbonyl] -4.6-dinitroanilino] ethyl methanesulfonate(48); Reaction of 37 as in Scheme 14, and chromatography on silica gel, eluting with EtOAc/petroleum ether (2:1) gave a product that was precipitated from a CH2Cl2 solution with i-Pr2O to give 2-[(2-bromoethyl)-2,4-dinitro-6-[[[2,3,4,6-tetra-O-acetyl-beta-D- gulopyranosyl)oxy] ethyl] amino] carbonyl] anilino] ethyl methanesulfonate (47) (2.04 g, 82%) as a yellow solid: mp 70-73 0C; 1H NMR [(CD3)2SO] delta 8.84 (t, / = 5.5 Hz, 1 H), 8.75 (d, / = 2.8 Hz, 1 H), 8.31 (dj = 2.8 Hz, 1 H), 5.27 (d, J = 3.2 Hz, 1 H), 5.17 ‘(ddj = 10.4, 3.5 Hz, 1 H), 4.99 (ddj = 10.3, 8.0 Hz, 1 H), 4.78 (dj = 8.0 Hz, 1 H), 4.28 (tj = 5.4 Hz, 1 H), 4.22 (tj = 6.5 Hz, 1 H), 4.11-3.99 (m, 2 H), 3.94-3.84 (m, 1 H), 3.77-3.68 (m, 1 H), 3.63-3.37 (m, 8 H), 3.13 (s, 3 H), 2.13 (s, 3 H), 2.01 (s, 3 H), 1.97 (s, 3 H), 1.92 (s, 3 H. 13C NMR [(CD3)2SO] delta 169.8, 169.7, 169.4, 169.1, 165.4, 145.8, 145.3, 140.8, 135.8, 127.4, 122.3, 100.1, 70.2, 69.9, 68.5, 67.4, 67.3 (2), 61.2, 54.3, 51.1, 39.4, 36.4, 29.7, 20.4, 20.3, 20.2 (2).

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, 1072-52-2, 2-(Aziridin-1-yl)ethanol.

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; WO2008/30112; (2008); 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. 15852-73-0, name is (3-Bromophenyl)methanol. A new synthetic method of this compound is introduced below., Recommanded Product: 15852-73-0

Example 50 {[(3-Bromophenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane TBSCl (18.7 g, 124.3 mmol), Et3N (14.08 g, 139.2 mmol) and DMAP (194.3 mg, 8.9 mmol) were dissolved in CH2Cl2 (120 mL) and the solution was cooled to 0-5 C. (3-Bromophenyl)methanol (18.5 g, 99.4 mmol) was added dropwise to the solution. After the addition of the (3-bromophenyl)methanol, the mixture was warmed to room temperature and stirred for 2 h. 5% HCl was added to the reaction mixture to adjust the pH=4-5. Then the organic phase was separated and the aqueous layer was extracted with CH2Cl2 (50 mL*2). The combined organic phases were washed with water and dried over Na2SO4. After removing the solvent, 28.5 g of {[(3-bromophenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane was obtained (Yield: 95.1%).

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, 15852-73-0, (3-Bromophenyl)methanol.

Reference:
Patent; Glaxo Group Limited; US2009/203677; (2009); A1;,
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Related Products of 31775-67-4 ,Some common heterocyclic compound, 31775-67-4, molecular formula is C5H12ClNO, 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 1-(4-fluorobenzyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (Intermediate 20), (110 mg) in DMF (2.1 mL) stirred at rt under nitrogen was added HATU (248 mg) and TEA (0.11 mL). This mixture was left to stir for 15 minutes and then trans-2-aminocyclopentanol hydrochloride (56.0 mg) was introduced. The reaction was left to stir overnight at room temperature, at which point LC-MS indicated completion. The reaction mixture was transferred to a separating flask and EtOAc and water were added. The phases were separated and the aqueous phase was extracted twice more with ethyl acetate. The organic phases were combined, washed with brine and the solvent was removed in vacuo. The residue was purified by column chromatography (normal phase, 25 g, Biotage SNAP cartridge KP-Sil, 25 mL per min, gradient 0% to 100% EtOAc in hexane, followed by 0-15% MeOH/EtOAc) to give the desired product as a racemic mixture of trans isomers (65 mg). LCMS: m/z 354.57 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.64-1.91 (m, 4H) 1.97-2.15 (m, 1H) 2.17-2.35 (m, 1H) 4.05-4.22 (m, 2H) 5.29 (s, 2H) 6.93-7.22 (m, 5H) 7.59 (d, J=8.3 Hz, 1H) 8.09 (s, 1H) 8.48 (d, J=4.7 Hz, 1H) 9.11 (d, J=3.1 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31775-67-4, its application will become more common.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; PAYNE, Andrew; CASTRO PINEIRO, Jose Luis; BIRCH, Louise Michelle; KHAN, Afzal; BRAUNTON, Alan James; KITULAGODA, James Edward; SOEJIMA, Motohiro; WO2015/49574; (2015); A1;,
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Electric Literature of 626-18-6, 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. 626-18-6, name is 1,3-Benzenedimethanol. A new synthetic method of this compound is introduced below.

Example 6Direct Single-Stage Amination of Alcohols andHydroxy Acids by Means of Ammonia Over aHomogeneous Ruthenium Catalyst and Xantphos ata high V7J Vgas (according to the invention)Under an argon atmosphere, m g of starting material, mRU g of [carbonylchlorohydridotris(triphenylphosphane)ruthenium(II)] and mp g of 9,9-dimethyl-4,5-bis (diphenylphosphino)xanthene as catalyst and V07 ml of 2-methyl-2-butanol as solvent were introduced into a 50 mlsteel tube. The vessel was closed, pressurized three times with 20 bar of argon and depressurized each time. The vessel was then cooled by means of dry ice and m g of ammonia were condensed in. The reactor is heated to T C. and maintained at this temperature for 20 hours. Afier cooling to room temperature, the reactor was depressurized and opened, the solvent was removed on a rotary evaporator and the residue was dissolved in methanol and then analysed by gas chromatography. Reaction parameters and conversions and selectivities to the desired reaction product are shown in Tab. 5. The results show that many different hydroxy-thnctionalized substrates can be aminated by the method described.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,626-18-6, 1,3-Benzenedimethanol, and friends who are interested can also refer to it.

Reference:
Patent; EVONIK DEGUSSA GmbH; Klasovsky, Florian; Tacke, Thomas; Pfeffer, Jan Christoph; Haas, Thomas; Beller, Matthias; Martin, Andreas; Deutsch, Jens; Koeckritz, Angela; Imm, Sebastian; Haberland, Juergen; US2013/331580; (2013); A1;,
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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. 17701-61-0, name is Benzyl 3-hydroxy-2,2-dimethylpropanoate, molecular formula is C12H16O3, 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: 17701-61-0

tert-Butyl phthalate (5.38 g) was dissolved in toluene (50 ml). To this solution were successively added triethylamine (3.7 ml) and diphenylphosphoryl azide (5.7 ml) and the mixture was heated to 130C and stirred for 1 hr. The reaction mixture was allowed to cool to room temperature and 3-hydroxy-2,2-dimethylpropionic acid benzyl ester obtained in Example 1-4 a) (4.95 g) was added. The mixture was stirred at room temperature for 17 hr. The reaction mixture was diluted with ethyl acetate (50 ml), washed successively with water (50 ml) and saturated aqueous sodium chloride solution (5 ml), dried and concentrated under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (n-hexane/ethyl acetate=1:1). The oily substance (3.28 g) after purification was dissolved in dichloromethane (30 ml). This solution was cooled to 0C and trifluoroacetic acid (30 ml) was added. The mixture was heated to room temperature and stirred for 3 hr. The reaction mixture was concentrated under reduced pressure, after which water (50 ml) was added, and the mixture was extracted with ethyl acetate (150 ml). The organic layer was washed successively with water (50 ml×3) and saturated aqueous sodium chloride solution (50 ml), dried and concentrated under reduced pressure. The obtained oily substance was purified by column chromatography to give the title compound (2.54 g, yield 89%) as a colorless oil.1H-NMR(delta, 300MHz, DMSO-d6) 1.22(6H,s),4.20(2H,s), 5.13(2H,s),7.12(1H,m),7.25-7.34 (5H,m),7.60(1H,m), 7.99(1H,dd,J=1.6,7.9Hz),8.23(1H,d,J=7.9Hz),10.72(1H,s),13.63(1 H,brs).

With the rapid development of chemical substances, we look forward to future research findings about 17701-61-0.

Reference:
Patent; Japan Tobacco Inc.; EP1452526; (2004); A1;,
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Synthetic Route of 25574-11-2, Adding some certain compound to certain chemical reactions, such as: 25574-11-2, name is 3-(4-Bromophenyl)propan-1-ol,molecular formula is C9H11BrO, 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 25574-11-2.

Example A.4: Synthesis of 3-(4-bromophenyl)propanal (10*) Alcohol 4* (4.71g, 21.8mmol) was dissolved in DCM, treated with Dess-Martin periodinane (9.71g, 20.9mmol) and stirred at rt for 2h. The mixture was quenchedwith 2M NaOH, the phases were separated the aqueous layer extracted with DCM. The combined organic phases were dried on Mg504, filtered and evaporated in vacuo. The crude was purified by flash chromatography on silica gel using a gradient of DCM in cHex to yield the desired product 10* (4.46g, 96%) as a colourless liquid.1H NMR (400MHz, CDCI3) 6 9.81 (5, 1H), 7.41 (d, 2H), 7.07 (d, 2H), 2.91 (t, 2H),2.79-2.74 (m, 2H).MS (ES) C9H9BrO requires: 211/213, (Mi-H) not found, 100%.

According to the analysis of related databases, 25574-11-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEAD DISCOVERY CENTER GMBH; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; WALDMANN, Herbert; DI LUCREZIA, Raffaella; NUSSBAUMER, Peter; KOCH, Uwe; MENNINGER, Sascha; CHOIDAS, Axel; KLEBL, Bert M.; WO2015/181272; (2015); A1;,
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