Category: alcohols-buliding-blocks

Application of 42142-52-9 ,Some common heterocyclic compound, 42142-52-9, molecular formula is C10H15NO, 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.

250 milliliters of N,N-dimethylacetamide was taken into round bottom flask to which 115.3 grams of potassium tertiary butoxide, 100 grams of N-Methyl-3-phenyl-3-(o-tolyloxy)propylamine and 100 grams of 2-fluorotoulene were added,followed by heating to 120 to 130C for about 12 to 14 hours. Solvent was distilled from the above reaction mass under vacuum below 118 to 122C, followed by the addition of 500 milliliters of methanol and 300 milliliters of a 45-50 percent by weight sodium hydroxide solution. The reaction mass was transferred into an autoclave and then heated to a temperature of 105 to 110C for about 6 to 7 hours. The solvent was totally distilled off under vacuum at a temperature below 80C, then 1 liter of demineralised water and 1 liter of toluene were added, followed by cooling to 0 to 5C and adjusting the pH to a value between 8 and 9 with dilute hydrochloric acid. The above reaction mass was stirred for about 15 to 30 minutes to separate the organic and aqueous layers and the aqueous layer was extracted with 400 milliliters of toluene followed by stirring for about 5 to 10 minutes. Organic and aqueous layers were separated and the combined organic layers were washed with 400 milliliters of dimineralised water. The organic layer was taken into a round bottom flask followed by complete distillation under vacuum below 80C and then cooled to 25 to 35C. 1.3 liters of acetone and 64.2 grams of oxalic acid were added to the round bottom flask followed by stirring for about 45 to 60 minutes. The solid mass that was obtained was filtered and washed with 520 milliliters of acetone, and then slurried in 700 milliliters of acetonitrile in a round bottom flask and stirred for about 30 to 45 minutes. The solid mass was isolated by filtration and washed with 200 milliliters of acetonitrile, followed by drying at 50 to 60C for 4 to 5 hours under vacuum to afford atomoxetine oxalate.

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. 42142-52-9, 3-(Methylamino)-1-phenylpropan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; WO2006/9884; (2006); A1;,
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Reference of 5299-60-5, 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.5299-60-5, name is Ethyl 6-hydroxyhexanoate, molecular formula is C8H16O3, molecular weight is 160.21, as common compound, the synthetic route is as follows.

The PCC (16.20g, 75 . 50mmol) dissolved in dichloromethane (140 ml) in, lowering the temperature to 0 C, dropping 6 – hydroxy hexanoic acid ester (10.30g, 64 . 30mmol) of dichloromethane (20 ml) solution. Heating the reaction to room temperature, stirring the reaction 2 hours, adding ethyl acetate (100 ml), filtered, the filtrate is concentrated. The residue by silica gel column chromatography (petroleum ether/ethyl acetate (v/v)=10/1) to obtain the title compound as white solid (9.28g, 45.0%).

Statistics shows that 5299-60-5 is playing an increasingly important role. we look forward to future research findings about Ethyl 6-hydroxyhexanoate.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Gao Jinheng; Zhang Yingjun; (37 pag.)CN106279153; (2017); A;,
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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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Adding a certain compound to certain chemical reactions, such as: 329218-12-4, 3-Bromo-4-chlorobenzyl Alcohol, 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, 329218-12-4, blongs to alcohols-buliding-blocks compound. Formula: C7H6BrClO

Example 12 4-Aminomethyl-cyclohexanecarboxylic acid {1-[3-(3-amino-1H-indazol-6-yl)-4-chloro-phenyl]-2-phenyl-ethyl}-amide 12A. 3-Bromo-4-chloro-benzaldehyde: To a cooled (0 C.), clear, colorless solution of 3-bromo-4-chlorobenzoic acid (1.0 g, 4.25 mmol) in THF (43 mL) was added dropwise a 1.0 M borane-THF complex (12.7 mL, 12.7 mmol). After 15 min, the reaction was warmed to rt and then to reflux. After 2 h, the reaction was cooled to rt, then to 0 C., and then quenched with MeOH (10 mL). The reaction was warmed to rt and after 15 min., the reaction was concentrated. The residue was dissolved in EtOAc and washed with 1.0 N HCl, sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated to give a clear, colorless liquid. The liquid was dissolved in CH2Cl2 (17 mL) and cooled to 0 C. Next Dess-Martin periodinane (2.16 g, 5.10 mmol) was added. The resulting cloudy pale orange suspension was stirred for 30 min. and then diluted with Et2O (50 mL). The reaction was filtered through a plug of silica gel and the filtrate was concentrated to give an off-white solid. Column chromatography on silica gel (gradient elution 0-25% EtOAc in Hex) gave 0.815 g (87%) of the aldehyde as a white solid. 1H NMR (400 MHz, CDCl3) delta: 9.94 (s, 1H), 8.13 (d, J=1.8 Hz, 1H), 7.77 (dd, J=8.1, 2.0 Hz, 1H), 7.63 (d, J=7.9 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,329218-12-4, its application will become more common.

Reference:
Patent; Corte, James R.; Quan, Mimi L.; Smallheer, Joanne M.; Pinto, Donald J.; US2006/154915; (2006); A1;,
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Reference of 52273-77-5, 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 52273-77-5, name is 2-(3-Aminophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Step B: 2-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]ethanol Into a reaction flask were added 2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine (0.33 g, 1.2 mmol) (prepared according to Example 1, step A), 1,4-dioxane (20 mL), 2-(3-aminophenyl)ethanol (0.22 g, 1.6 mmol), and p-toluenesulfonic acid monohydrate (0.080 g, 0.42 mmol). The mixture was heated at 105 C. for 3 hours and then an aqueous solution of NaHCO3 (saturated) was added. The organic solvent was removed under vacuum followed by the addition of water and EtOAc. The aqueous layer was extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4, and concentrated under vacuum. The crude was purified by silica gel column chromatography to provide the desired product as a white solid (0.33 g, 74% yield). LCMS for C20H22ClN4O2 (M+H)+: m/z=385.1.

According to the analysis of related databases, 52273-77-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; US2010/190804; (2010); 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.928-51-8, name is 4-Chlorobutan-1-ol, molecular formula is C4H9ClO, molecular weight is 108.5667, as common compound, the synthetic route is as follows.name: 4-Chlorobutan-1-ol

To a suspension of 4-ethynyl-1H-pyrazole (920 mg, 10 mmol) and4-chlorobutan- 1-ol (216 mg, 20 mmol) in acetonitrile (25 mL) was added K2C03 (4.1 g,30 mmol, 3 eq) and KI (166 mg, 1 mmol, 0.1 eq). The mixture was stirred for 6 hours at85 C under N2 protection. The readion mixture was quenched with water and extractedwith EtOAc. The residue was purified by chromatography (DCM:MeOH 10:1) to afford to afford 1.3 g of 4-(4-ethynyl-1H-pyrazol-1-yl)butan-1-ol with 80% yield. ESI-MS mlz 165.02 [M+Hjt

At the same time, in my other blogs, there are other synthetic methods of this type of compound,928-51-8, 4-Chlorobutan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; WANG, Shaomeng; HU, Yang; QIN, Chong; XU, Fuming; HU, Jiantao; XIANG, Weiguo; ZHOU, Bing; (233 pag.)WO2018/52949; (2018); A1;,
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Application of 495-76-1, 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. 495-76-1, name is Benzo[d][1,3]dioxol-5-ylmethanol. A new synthetic method of this compound is introduced below.

To a round-bottomed flask were added piperonyl alcohol (4) (2 mmol, 304 mg) and dichloromethane (20 mL). The mixture was cooled to 0 oC under stirring and anhydrous conditions. Then, a solution of phosphorus tribromide (10 mmol, 2.71 g, 0.9 mL) in dichloromethane (9.1 mL) was added dropwise using syringe and needle. The reaction was maintained under stirring and anhydrous conditions at room temperature for 3 h. Afterwards, distilled water (50 mL) was added to the mixture, which was extracted with CH2Cl2 (3 x 50 mL). The organic phase was dried over MgSO4. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using hexane/ethyl acetate (10:1) as eluent to afford the desired product 3. Yield: 371 mg (86%); off-white solid; m.p. 40-41 oC (m.p. lit.11 39 oC); Rf = 0.44 (eluent: hexane/ethyl acetate (10:1)); 1H NMR (300 MHz, CDCl3): delta 6.85 (d, J = 8.7 Hz, 2H), 6.74 (d, J = 7.9 Hz, 2H), 5.96 (s, 2H), 4.45 (s, 2H); 13C NMR (75 MHz, CDCl3): delta 147.9, 147.8, 131.5, 122.7, 109.4, 108.3, 101.3, 34.2; IR (KBr, cm-1) 3448.7, 2900.9, 1500.6, 1485.2, 1251.8; GC/MS (m/z, %): 214 (10.0), 215 (9.9), 135 (100.0), 77 (23.8), 51 (16.3), 105 (7.0).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,495-76-1, Benzo[d][1,3]dioxol-5-ylmethanol, and friends who are interested can also refer to it.

Reference:
Article; Correa, Bianca K.; Silva, Tamiris R.C.; Raminelli, Cristiano; Tetrahedron Letters; vol. 59; 39; (2018); p. 3583 – 3585;,
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Reference of 10029-04-6 , The common heterocyclic compound, 10029-04-6, name is Ethyl 2-(hydroxymethyl)acrylate, molecular formula is C6H10O3, 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 2-hydroxymethyl-acrylic acid ethyl ester (260 mg, 2 mmol) and imidazole (163 mg, 2.4 mmol) in dry DMF (5 ml) was added tert- butyldimethylsily. chloride (362 mg, 2.4 mmol). The reaction mixture was stirred overnight and diluted with ether, washed with water three times and dried over MgSO4. Solvent was removed under reduced pressure to provide a crude product that was purified by column chromatography using a solution of ethyl acetate in hexanes (1 :6) to obtain the title product (463 mg, 95%).

The synthetic route of 10029-04-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2007/97937; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 33420-52-9, 2,2-Difluoropropan-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, 33420-52-9, blongs to alcohols-buliding-blocks compound. SDS of cas: 33420-52-9

To a solution of 2,2-difluoropropan-1-ol (I-10A-7b; 1.76 g, 18.3 mmol), dimethylaminopropylamine (DMAP: 157 mg, 1.3 mmol), and triethylamine (2.20 g, 3.1 ml, 22 mmol) in CH2Cl2 (15 ml) at 0 C. was added triflic anhydride (Tf2O; 6.2 g, 3.7 ml, 22 mmol). The reaction mixture initially turned a pink color, then a yellow color following the complete addition of Tf2O. The reaction mixture was stirred at 0 C. for 2 hours and diluted with CH2Cl2. The organic solution was washed with water, 1 M aqueous citric acid, and saturated aqueous NaHCO3, dried, and concentrated under reduced pressure (225 mm/Hg; bath temperature -30 C.) to give the desired product, trifluoromethanesulfonic acid 2,2-difluoropropyl ester (I-10A-7c), as a pink oil (3 g, 72%): 1H NMR (400 MHz, CDCl3) delta 4.49 (t, J=10.8 Hz, 2H), 1.74 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,33420-52-9, its application will become more common.

Reference:
Patent; Pfizer Inc.; US2004/214837; (2004); 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. 7314-44-5, name is (2,4-Dimethoxyphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: (2,4-Dimethoxyphenyl)methanol

General procedure: In a 10 cm3 flask, 50 mg of phosphine-polyphosphazene(0.094 mmol) was dissolved in 3 cm3 anhydrous CH2Cl2 under an argon atmosphere. The resulting solution was cooled to 0 C and a solution of 0.384 mmol C2Cl6 In a 10 cm3 flask, 50 mg of phosphine-polyphosphazene(0.094 mmol) was dissolved in 3 cm3 anhydrous CH2Cl2 under an argon atmosphere. The resulting solution was cooled to 0 C and a solution of 0.384 mmol C2Cl6 in 1 cm3 anhydrous CH2Cl2 was added followed by 0.094 mmol ofthe alcohol after 5 min. After further stirring for 15 min the solvent was removed, the residue was taken up in a minimum amount of CHCl3 and the oxidized polymer was precipitated in an appropriate solvent. The polymer was removed by filtration, and washed with the precipitation solvent. The combined filtrates were evaporated to dryness and dried under high vacuum to yield the corresponding alkyl orbenzyl chlorides. in 1 cm3 anhydrous CH2Cl2 was added followed by 0.094 mmol ofthe alcohol after 5 min. After further stirring for 15 min the solvent was removed, the residue was taken up in a minimum amount of CHCl3 and the oxidized polymer was precipitated in an appropriate solvent. The polymer was removed by filtration, and washed with the precipitation solvent. The combined filtrates were evaporated to dryness and dried under high vacuum to yield the corresponding alkyl orbenzyl chlorides.

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, 7314-44-5, (2,4-Dimethoxyphenyl)methanol.

Reference:
Article; Koenig, Michael; Linhardt, Anne; Brueggemann, Oliver; Teasdale, Ian; Monatshefte fur Chemie; vol. 147; 9; (2016); p. 1575 – 1582;,
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