Category: alcohols-buliding-blocks

Electric Literature of 29908-11-0, 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. 29908-11-0, name is (1,4-Dioxan-2-yl)methanol. A new synthetic method of this compound is introduced below.

To a solution of(l, 4-dioxan-2-yl) methanol (2.4 g) in dimethylsulfoxide (24 mL) was added 5-bromo-2-chloropyridine (3.91 g) and sodium hydride (0.81 g) at 20 C under nitrogen flow. Thereaction mixture was stirred at 60 C for 10 hours under nitrogen atmosphere. The reaction was diluted with water (40 mL) at 25 C and extracted with ethyl acetate (3 x 40 mL). The combined organic layers were washed with brine (5 x 20 mL) and dried over sodium sulfate. After filtration, the filtrate was concentrated to give a residue which was purified by colunm chromatography on silica gel (eluted with petroleum ether:ethyl acetate = 100:1 to 20:1) to give the title compound. ?H NMR (400 MHz, CDC13) 6ppm 8.15 (d, 1H), 7.63 (dd, 1H), 6.70 (d, 111) 4.38-4.49 (m, 2H), 3.78-3.85 (m, 2H), 3.59-3.71 (m, 6H),3.52 (dd, 2H), 3.35 (s, 311).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29908-11-0, its application will become more common.

Reference:
Patent; ABBVIE INC.; ABBVIE DEUTSCHLAND GMBH & CO. KG; BRAJE, Wilfried; DOHERTY, George; JANTOS, Katja; JI, Cheng; JUDD, Andrew; KUNZER, Aaron; MASTRACCHIO, Anthony; SONG, Xiaohong; SOUERS, Andrew; SULLIVAN, Gerard; TAO, Zhi-Fu; TESKE, Jesse; WANG, Xilu; WENDT, Michael; PENNING, Thomas; LAI, Chunqui; KLING, Andreas; POHLKI, Frauke; (197 pag.)WO2019/35911; (2019); A1;,
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Reference of 929-06-6, 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. 929-06-6, name is 2-(2-Aminoethoxy)ethanol, molecular formula is C4H11NO2, 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.

a) [2-(2-Hydroxy-ethoxy)-ethyl]-carbamic acid terf-butyl esterTo a solution of 2-(2-amino-ethoxy)-ethanol (5.00 g) in water (35 mL) at 00C potassium hydroxide (2.93 g) was added. To this mixture maintained at O0C, a solution of d-tert- butyldicarbonate (11.40 g) in dioxane (17 mL) was added dropwise. The resulting mixture was stirred at 00C for 1 h and then 4 h at room temperature. Dioxane was evaporated under reduced pressure and the aqueous solution was extracted with DCM (2 x 25 mL). The organic phase was dried and evaporated under reduced pressure. The residue was purified by flash chromatography (silica gel, EtOAc / petroleum ether 40 /60 to 60 / 40) to give the title compound (8.50 g); ESMS m/z 205.3 [M+H]+.

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 929-06-6, 2-(2-Aminoethoxy)ethanol.

Reference:
Patent; GLAXO GROUP LIMITED; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2006/50942; (2006); A1;,
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Electric Literature of 10488-69-4, 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.10488-69-4, name is Ethyl 4-chloro-3-hydroxybutanoate, molecular formula is C6H11ClO3, molecular weight is 166.6, as common compound, the synthetic route is as follows.

Example 5; [68] 41.0 g (1.084 mol) of sodium borohydride and 200 g (1.205 mol, 99.3percent ee) of ethyl (S)-4-chloro-3-hydroxybutyrate were dissolved in 400 g of tetrahydrofuran, and 34.7 g (1.084 mol) of methanol was added dropwise at room temperature for 1 hour. After stirring at room temperature for 10 hours, the reaction mixture was cooled below 1O0C. Then, after adding 122 g of 36percent HCl dropwise, the solvent was removed by distillation under reduced pressure below 4O0C. Using 550 mL of methanol, concentration under reduced pressure was performed for 3 times below 4O0C. 550 mL of di- chloromethane and 20 g of Na2SO4 were added to the resultant residue, and stirring was performed for 30 minutes. After filtering off solid inorganic materials and removing the solvent under reduced pressure, 144 g of (S)-4-chloro-l,3-butanediol was obtained as oil (yield = 96percent).

The chemical industry reduces the impact on the environment during synthesis 10488-69-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; RSTECH CORPORATION; WO2008/93955; (2008); A1;,
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Electric Literature of 52059-53-7, 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.52059-53-7, name is 2-(3-Fluorophenyl)ethanol, molecular formula is C8H9FO, molecular weight is 140.1549, as common compound, the synthetic route is as follows.

General procedure: In a dry sealed tube under argon were placed11b(0.56 mmol), 3-fluorobenzyl alcohol (1.68 mmol), cesium carbonate (0.84 mmol), copper iodide (0.056 mmol) (or copper(I) oxide), 1,10-phenanthroline (0.11 mmol) (or 3,4,7,8-tetramethyl-1,10-phenanthroline) in toluene (1.1 mL) and the mixture was heated at 130 C for 20 h. After completion of the reaction (monitored by TLC), the mixture was then cooled at room temperature and it was quenched with saturated aqueous NH4Cl (3 ¡Á 50 mL), extracted with EtOAc. The organic layers were dried over anhydrous MgSO4and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (EtOAc: Acetone: Hexane = 1:1:15) to afford intermediatepre-9h. To a solution of methyl piperazine carboxylatepre-9h(0.136 mmol) in dichloromethane (1.3 mL) was added trifluoroacetic acid (0.21 mL). The mixture was allowed to stir at 0 C for 3 h. After completion of the reaction (monitored by TLC), then neutralized by sodium hydrogen carbonate until the mixture to be pH 8 and extracted with EtOAc. The organic layers were dried over anhydrous MgSO4and concentrated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (MeOH:DCM = 1:15) to afford pyrimidine9h, which was isolated as HCl salt form after treating with 4 M HCl in diethyl ether.

Statistics shows that 52059-53-7 is playing an increasingly important role. we look forward to future research findings about 2-(3-Fluorophenyl)ethanol.

Reference:
Article; Kim, Juhyeon; Kim, Yoon Jung; Londhe, Ashwini M.; Pae, Ae Nim; Choo, Hyunah; Kim, Hak Joong; Min, Sun-Joon; Molecules; vol. 24; 18; (2019);,
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Synthetic Route of 346-06-5 ,Some common heterocyclic compound, 346-06-5, molecular formula is C8H7F3O, 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.

the [(IPr)AuCl](6mg,0.01mmol,1mol%)AgOTf2.6mg,0.01mmol,1mol%Phenylacetylene (102mg, 1mmol), 1,4- dioxane (1ml) and water (36ul, 2equiv.) Were successively added to 5ml microwave tube.After the reaction mixture was microwaved at 120 reactor for one hour, cooled to room temperature.Thereto was added [Cp * IrCl2]2(8mg, 0.01mmol, 1mol%), potassium t-butoxide (112mg, 1mmol),2-trifluoromethylbenzyl alcohol (211mg, 1.2mmol).After the reaction mixture was microwaved at 130 reactor and then reacted for 2 hours, cooled to room temperature.Filtered, and solvent was removed by rotary evaporation, then purified by column chromatography (developing solvent: petroleum ether / ethyl acetate) to give the pure title compound Yield: 84%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,346-06-5, its application will become more common.

Reference:
Patent; Nanjing University of Science and Technology; Li, Feng; Ma, Juan; Qu, panpan; (15 pag.)CN104557500; (2016); B;,
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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.6153-05-5, name is (Z)-3-Methylpent-2-en-4-yn-1-ol, molecular formula is C6H8O, molecular weight is 96.13, as common compound, the synthetic route is as follows.Safety of (Z)-3-Methylpent-2-en-4-yn-1-ol

n-BuLi (4.2 mL, 10 mmol, 2.4 mol/L) was added dropwise to a solution of (Z)-3-methylpent-2-en-4-yn-1-ol (0.48 g, 5 mmol) in THF (10 mL) at ?78 ¡ãC under a N2 atmosphere, andthen the mixture was stirred for 1 h at ?78 ¡ãC. A solution of 4e (1.01 g, 5 mmol) in THF (5 mL) wasadded slowly, the mixture was stirred for 0.5 h at ?78 ¡ãC, and then it was warmed to room temperatureand stirred for 2 h. The reaction was quenched with saturated aqueous NH4Cl solution (10 mL) andextracted with EtOAc (3 ¡Á 30 mL). The combined organics were washed with brine (2 ¡Á 20 mL), driedover anhydrous Na2SO4 and concentrated. The residue was purified by silica gel columnchromatography (petroleum ether/EtOAc, 1:1) to afford 6i (1.40 g, 94percent) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6153-05-5, (Z)-3-Methylpent-2-en-4-yn-1-ol, and friends who are interested can also refer to it.

Reference:
Article; Han, Xiaoqiang; Wan, Chuan; Yang, Dongyan; Yuan, Xiaoyong; Du, Shijie; Xiao, Yumei; Qin, Zhaohai; Molecules; vol. 18; 9; (2013); p. 10776 – 10788;,
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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.

N- [3- (2-HYDROXYETHYL) PHENYL]-2, 4-DIMETHYL-1, 3-THIAZOLE-5-CARBOXAMIDE; 2- (3-Aminophenyl) ethanol (1.202 g, 8.76 MMOL) was added to a solution of 2, 4-dimethyl- 1, 3-thiazole-5-carboxylic acid (1.652 g, 10.51 MMOL), 1- (3-DIMETHYLAMINOPROPYL)-3- ethylcarbodiimide hydrochloride (2.015 g, 10.51 MMOL) and 1-hydroxybenzotriazole (1.420 g, 10.51 MMOL) in dry DMF (20 mL). The mixture was stirred for 14h then the DMF was removed under reduced pressure and the residue was partitioned between DCM and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel, eluting with ethyl acetate-cyclohexane (1: 1 to 1: 0) affording the title compound in 73% yield (1.772 g). MS; (ES) m/z: 277 [MH+]. C14H16N202S requires 276. 1H-NMR (300 MHz, D6-DMSO) S (ppm): 9.95 (s, 1H), 7.40-7. 50 (m, 2H), 7.19 (t, 1H), 6.92 (d, 1 H), 4.60 (t, 1 H), 5.57 (dd, 2H), 2.66 (t, 2H), 2.61 (s, 3H), 2.49 (s, 3H).

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; GLAXO GROUP LIMITED; WO2005/14552; (2005); A1;,
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Related Products of 14593-04-5 , The common heterocyclic compound, 14593-04-5, name is 3-Amino-3-phenyl-1-propanol, molecular formula is C9H13NO, 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.

a 4-Chloro-2-[(3-Hydroxy-1-Phenylpropyl)Amino]Benzonitrile A mixture of 3-amino-3-phenylpropanol (1 g, 6.6 mmol) and 4-chloro-2-fluorobenzonitrile (1 g, 6.4 mmol) in diisopropylethylamine (1.2 ml, 6.9 mmol) was heated at 140¡ã C. for 5 h. The crude reaction mixture was cooled to room temperature and applied to a silica column. The title compound was isolated as a colourless solid (1.1 g, 58percent) by elution with 20percent diethyl ether/isohexane. MS APCI+vem/z287 ([M+H]+).

The synthetic route of 14593-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cheshire, David; Connolly, Stephen; Cox, David; Millichip, Ian; US2003/73685; (2003); A1;,
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Application of 17100-58-2, 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 17100-58-2, name is (4-Bromo-2-methylphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Description 10: [2-methyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenyl]methanol (D10); 4-bromo-2-methyl-benzyl alcohol (D8f, 3Og, 150 mmol), bis(pinacolato)diboron (40 g, 156 mmol), Pd(dppf)CI2(ll) (8 g, 10 mmol), and potassium acetate (44 g, 448 mmol) were dissolved in 1 ,4-dioxane (600 ml_), and the reaction mixture was heated to reflux under N2 for 4 h. After cooling, the reaction mixture was filtered, and the filtrate was concentrated. Purification by column chromatography (silica gel; petroleum ether: ethyl acetate = 5:1 ) afforded the title compound as a red oil (34 g, yield: 90%). 1H NMR (400 MHz, DMSO-c/6) J7.50-7.38 (m, 3H), 5.14 (t, 1 H), 4.51 (d, 2H), 2.22 (s, 3H), 1.28 (s, 12H).

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; SMITHKLINE BEECHAM CORPORATION; WO2009/71504; (2009); A1;,
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Electric Literature of 34598-50-0 ,Some common heterocyclic compound, 34598-50-0, molecular formula is C9H9BrO, 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.

5-Bromo-1-indanol (1.0 g, 4.7 mmol) of Step A was dissolved in thionyl chloride (10 mL). After stirring at room temperature for 2 hrs, the solution was concentrated under vacuum. The residue was taken up in DMF (10 mL). To the mixture were added tert-butyl (3S)-3-methylpiperazine-1-carboxylate (0.94 g, 4.7 mmol), NaI (2 g, 13 mmol) and triethylamine (1.5 mL, 10 mmol). The resulting solution was stirred at 70 C. overnight. After cooling to room temperature, water was added. The solution was extracted with EtOAc twice. The combined EtOAc layers were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica (50% EtOAc in hexane) provided two isomers. Isomer 1 (fast moving isomer): 0.36 g; MS calculated for C19H27BrN2O2 (M+H)+ 395; found 395.1, 397.0. Isomer 2 (slow moving isomer): 0.33 g; MS found 395.1, 397.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,34598-50-0, its application will become more common.

Reference:
Patent; Xue, Chu-Biao; Cao, Ganfeng; Huang, Taisheng; Chen, Lihua; Zhang, Ke; Wang, Anlai; Meloni, David; Anand, Rajan; Glenn, Joseph; Metcalf, Brian W.; US2005/261310; (2005); A1;,
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