Month: January 2021

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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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 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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Electric Literature of 1462-03-9 , The common heterocyclic compound, 1462-03-9, name is 1-Methylcyclopentanol, molecular formula is C6H12O, 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.

[0375] 500 mg (3.87 mmol) of ethyl isocyanatoacetate was dissolved in 5 ml of dichloromethane. 0.05 ml of 4 N hydrochloric acid/1,4-dioxane solution was added to the obtained solution. 465 mg (4.64 mmol) of 1-methylcyclopentanol was added to the resultant mixture, and they were stirred for 3 hours 30 minutes. 10 ml of methanol and 12 ml of 1 N aqueous sodium hydroxide solution were added thereto and they were stirred for 15 minutes. The organic solvent was evaporated under reduced pressure. After extracting with dichloromethane twice, the aqueous layer was neutralized with 1 N aqueous hydrochloric acid solution. The product was extracted with dichloromethane 3 times and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain the title compound. The product was subjected to the next reaction without any purification. [0376] Yield: 43.0 mg (0.214 mmol), 5.5% 1H-NMR (CDCl3): (Only the main peaks are shown because the product contained impurities) 1.56 (3H, s), 5.22 (1H, d).

The synthetic route of 1462-03-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AJINOMOTO CO., INC.; US2004/167118; (2004); 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 455-01-6, name is 2-(3-(Trifluoromethyl)phenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows. name: 2-(3-(Trifluoromethyl)phenyl)ethanol

Example 85 3-(Trifluoromethyl)phenethyl N-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}carbamate 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (82 mg) was added to toluene/triethylamine = 10/1 (8 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (125 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 3-trifluoromethylphenethyl alcohol (70 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (68 mg, yield 45%). 1H-NMR (CDCl3, 400 MHz): 8.76 (1H, s), 8.01 (1H, s), 7.60 (1H, s), 7.43 – 7.58 (6H, m), 7.17 – 7.24 (2H, m),6.79 (1H, s), 4.44 (2H, t, J = 6.7 Hz), 4.17 (3H, s), 4.11 (3H, s), 3.08 (2H, t, J = 6.8 Hz) Mass spectrometry value (ESI-MS, m/z): 514 (M++1)

With the rapid development of chemical substances, we look forward to future research findings about 455-01-6.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1243582; (2002); A1;,
Alcohol – Wikipedia,
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Reference of 6920-22-5, 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. 6920-22-5, name is Hexane-1,2-diol. A new synthetic method of this compound is introduced below.

General procedure: To an oven dried 9mL screw cap tube, a magnetic stir-bar, diamine (0.5mmol), vicinal diol (1.5mmol), CsOH.H2O (0.375mmol), Co-phen/C-800 (1.5mol%) and toluene (2.5mL) were added under argon atmosphere. Then, the tube was sealed and placed in a preheated oil bath at 150C for 24h. After completion of the reaction, the tube was allowed to cool at room temperature. Then, the solvent was evaporated under reduced pressure. Finally, the product was purified by silica gel column chromatography using ethyl acetate/hexane as eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6920-22-5, Hexane-1,2-diol, and friends who are interested can also refer to it.

Reference:
Article; Panja, Dibyajyoti; Paul, Bhaskar; Balasubramaniam, Bhuvaneshwari; Gupta, Raju K.; Kundu, Sabuj; Catalysis Communications; vol. 137; (2020);,
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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. 178312-48-6, name is (4,4-Difluorocyclohexyl)methanol, the common compound, a new synthetic route is introduced below. Recommanded Product: (4,4-Difluorocyclohexyl)methanol

To a solution of the crude product of the previous step (465 mg, 0.31 mmol) and triethylenediamine (0.346 mg, 0.31 mmol) cooled to 0 C. in dichloromethane (20 mL) was added a p-toluenesulfonylchloride (0.589 g, 0.31 mmol) in dichloromethane (5 mL). The reaction mixture was stirred overnight and then washed with 0.5 N HCl (20 mL). The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by flash column chromatography to give the title compound as a white solid (748 mg).

The synthetic route of 178312-48-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Theravance, Inc.; US2009/62334; (2009); A1;,
Alcohol – Wikipedia,
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Application of 62285-58-9, 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 62285-58-9 as follows.

Following the general intermolecular amination procedure, 2,6-dimethylbenzyl alcohol (7q: 54 mg, 0.4 mmol), Du Bois’ catalyst (6.1 mg, 8.0 mumol), and 32 TsONHMe (0.121 g, 0.6 mmol) were stirred in TFE (4 mL) at 0 C. for 2 h. Chromatographic purification of the crude product afforded 14 (2,6-dimethyl-3-(methylamino)phenyl)methanol (8q: 28 mg, 42%) as a solid, mp 78.6 C. TLC: Rf?0.4 (40% EtOAc/hexanes); 1H NMR (400 MHz, CDCl3) delta 7.00 (d, J=8.2 Hz, 1H), 6.56 (d, J=8.2 Hz, 1H), 4.74 (s, 2H), 2.88 (s, 3H), 2.35 (s, 3H), 2.20 (s, 3H); 13C NMR (101 MHz, CDCl3) delta 145.88, 136.50, 128.53, 125.51, 121.93, 109.72, 59.77, 31.30, 19.13, 12.57. HRMS (ESI+) Calcd. for [C10H15NO+H]+ 166.1232, Found 166.1228.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62285-58-9, its application will become more common.

Reference:
Patent; The Board of Regents of the University of Texas System; William Marsh Rice University; FALCK, John R.; PAUDYAL, Mahesh P.; KUeRTI, Laszlo; (51 pag.)US2019/152892; (2019); A1;,
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Reference of 13674-16-3, 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 13674-16-3 as follows.

Step 4 (2R)-2-[4-(9-Bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-ethyl-phenoxy]3-phenyl-propionic acid methyl ester In a manner similar to the procedure of Example 49, Step 6 there was obtained from 4-(9-bromo-2,3-dimethyl-naphtho[2,3-b]thiophen-4-yl)-2-ethyl-phenol (0.45 g, 1.16 mmol), (S)-2-hydroxy-3-phenylpropionic acid, methyl ester (0.31 g, 1.72 mmol), triphenylphosphine (0.45 g, 1.72 mmol), diethylazodicarboxylate (0.27 mL, 1.71 mmol), and anhydrous benzene (5 mL) at 90 for 18 h the title compound as a glassy residue (0.22 g, 33%): NMR (DMSO-d6): delta8.22 (d, J=9 Hz, 1H), 7.66 (ddd, J=3, 6, 8 Hz, 1H), 7.59-7.22 (m, 7H), 7.20-7.02 (m, 2H), 6.92 (dd, J=2, 8 Hz, 1H), 5.31 (m, 1H), 3.74 and 3.70 (two s, atroph isomers, 3H), 3.32 (m, 2H), 2.64 (complex m, 2H), 2.45(s, 3H), 1.55 (s, 3H), 1.12 and 1.10 (two t, J=7 Hz, atroph isomers, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13674-16-3, its application will become more common.

Reference:
Patent; American Home Products Corporation; US6251936; (2001); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 624-95-3 ,Some common heterocyclic compound, 624-95-3, molecular formula is C6H14O, 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.

Dimethylsulfoxide (6.80 mL, 95.7 mmol) was added over 5 min to a solution of oxalylchloride (23.9 mL, 47.8 mmol) in dichloromethane at -78 0C. The resulting mixture was stirred at -78 0C for 5 min, then 3,3-dimethyl-butan-l-ol (5.22 mL, 43.1 mmol) was added. After stirring an additional 30 min at -78 0C, triethylamine (23.3 mL, 167 mmol) was added and the reaction mixture warmed to 0 0C and stirred at that temperature for 45 min. The mixture was then transferred to a separatory funnel and was washed with 0.5 M aqueous hydrochloric acid. The organic layer was dried over sodium sulfate, filtered and was concentrated in vacuo to a volume of about 70 mL (water bath temperature = 0 0C). Methanol (100 mL) was added followed sequentially by 1 -amino- lH-pyrrole-2-carboxylic acid allyl ester (Example Ib, 7.16 g, 43.1 mmol), acetic acid (6 mL), and sodium cyanoborohydride (5.42 g, 86.3 mmol). The reaction mixture was stirred at 23 0C for 2 h, and then was partitioned between saturated aqueous sodium bicarbonate solution (400 mL) and a 1 : 1 mixture of ethyl acetate and hexanes (2 x 200 mL). The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (Merck silica gel 60, 40-63 mum, 5?10% ethyl acetate in hexanes) afforded the desired product, l-(3,3-dimethyl-butylamino)-lH-pyrrole-2- carboxylic acid allyl ester (4.04 g, 16.15 mmol, 37% yield) as a clear liquid. 1H NMR (400 MHz, CDCl3) delta: 0.91 (9H, s), 1.42 – 1.46 (2H, m), 2.98 – 3.04 (2H, m), 4.75 – 4.77 (2H, m), 5.26 – 5.28 (IH, m), 5.37 – 5.41 (IH, m), 5.96 – 5.99 (IH, m), 6.01 – 6.05 (IH, m), 6.27 – 6.30 (IH, m), 6.89 – 6.91 (IH, m), 6.96 – 6.98 (IH, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,624-95-3, its application will become more common.

Reference:
Patent; ANADYS PHARMACEUTICALS, INC.; WO2007/150001; (2007); A1;,
Alcohol – Wikipedia,
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