Tag: M.W=100-200

Application of 3068-00-6, 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. 3068-00-6, name is 1,2,4-Butanetriol. A new synthetic method of this compound is introduced below.

To neat butane- 1 ,2,4-triol (300 g, 2.83 mol) was added 4- methylbenzenesulfonic acid (10 g, 58 mmol). The reaction mixture was heated to 180C. After 2 hours, the reaction mixture was cooled to ambient temperature and tetrahydrofuran-3-ol was afforded by distillation of the mixture under reduced pressure (10 mm Hg; the product fraction was collected at 46C).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3068-00-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; BIENSTOCK, Corey, E.; BUTCHER, John, W.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; DONOFRIO, Anthony; ELLIS, John Michael; FISCHER, Christian; HAIDLE, Andrew, M.; JEWELL, James, P.; KNOWLES, Sandra Lee; NORTHRUP, Alan, B.; OTTE, Ryan, D.; PETERSON, Scott, L.; SMITH, Graham Frank; WO2013/52394; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 765-04-8, 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 765-04-8, name is Undecane-1,11-diol. This compound has unique chemical properties. The synthetic route is as follows.

A solution of undecane-1,11-diol (14; 1.883 g, 10.00 mmol, 1.00 equiv) in CH2Cl2 (50 mL) at r.t. was treated with TBSCl (1.658 g, 11.00 mmol, 1.10 equiv) and imidazole (1.021 g, 15.00 mmol, 1.50 equiv). The suspension was stirred for 16 h at this temperature, water (25 mL) was added, and the mixture was extracted with CH2Cl2 (3 25 mL). The combined organic phases were washed with water, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The remaining residue was purified by column chromatography (cyclohexane/EtOAc, 9:1) to afford the title compound. Yield: 1.641 g (5.424 mmol, 54%); colourless oil; Rf = 0.55 (cyclohexane/ EtOAc, 3:1). IR (ATR): 3362, 2926, 2855, 1470, 1463, 1388, 1361, 1254, 1098, 1056, 1006, 939, 833, 815, 773, 721, 661 cm-1. 1H NMR (CDCl3, 500 MHz): delta = 3.63 (dt, J = 5.5, 6.5 Hz, 2 H, 1-H), 3.59 (t, J = 6.7 Hz, 2 H, 11-H), 1.60-1.47 (m, 4 H, 2-H, 10-H), 1.38-1.21 (m, 15 H, 3-H to 9-H, OH), 0.89 (s, 9 H, tBu), 0.04 (s, 6 H, Me). 13C NMR (CDCl3, 125 MHz): delta = 63.5, 63.3, 33.03, 32.96, 29.76, 29.74, 29.67, 29.58, 29.57, 26.1, 25.94, 25.88, 18.5, -5.1. HRMS (ESI): m/z [M + H]+ calcd for C17H39O2Si: 303.27138; found: 303.27159.

According to the analysis of related databases, 765-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Petermichl, Markus; Steinert, Christine; Schobert, Rainer; Synthesis; vol. 51; 3; (2019); p. 730 – 738;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 3562-73-0 ,Some common heterocyclic compound, 3562-73-0, molecular formula is C14H14O, 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: A mixture of 1-phenethyl alcohol (1.0 mmol), N-(phenyl)phenylalanine(0.0241 g, 0.1 mmol), CuBr2 (0.0223 g, 0.1 mmol),NaOAc (0.1640 g, 2.0 mmol), TEMPO (0.0156 g, 0.1 mmol), andH2O (3.0 mL) were placed into a 100 mL Schlenk tube, whichwas vigorously stirred in air under reflux for 12 h. After thereaction, the product was extracted with CH2Cl2 (3 ¡Á 2.0 mL).The combined organic phase was washed with H2O (3.0 mL) anddried over anhydrous MgSO4. After concentration undervacuum, the residue was purified by column chromatography toafford acetophenone.Isolated yield: 0.1080 g (90%).

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. 3562-73-0, 1-(4-Biphenylyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Guofu; Lei, Jie; Han, Xingwang; Luan, Yuxin; Ding, Chengrong; Shan, Shang; Synlett; vol. 26; 6; (2015); p. 779 – 784;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 7287-81-2, 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. 7287-81-2, name is 1-(m-Tolyl)ethanol. A new synthetic method of this compound is introduced below.

General procedure: In a flask under argon atmosphere, iridium catalyst 5 (0.50 or 1.0 mol %), sodium hydroxide (0.50 or 1.0 mol %), water (2 mL), and alcohol (2.0 mmol) were placed. The mixture was stirred under vigorous reflux (temperature of the oil bath was set at 140 C) for 20-96 h. After cooling to room temperature, water (4 mL) was added and the mixture was transferred to a separate funnel. Extraction of the organic compounds with dichloromethane (15 mL x 3), dehydration with sodium sulfate, followed by evaporation under vacuum gave crude mixture. For entries 2-11,the conversion of starting alcohol and the yield of ketone were determined by 1H NMR analysis in chloroform-d using triphenylmethane as an internal standard. For entries 1 and 12-14, the conversion of starting alcohol and the yield of ketone were determined by GC analysis using biphenyl as an internal standard. For entries 2-8, 10, and 11, the product was isolated by silica-gel column chromatography (eluent:ethyl acetate/ hexane).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7287-81-2, 1-(m-Tolyl)ethanol, and friends who are interested can also refer to it.

Reference:
Article; Toyomura, Kazuki; Fujita, Ken-Ichi; Chemistry Letters; vol. 46; 6; (2017); p. 808 – 810;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 431-38-9, 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.431-38-9, name is 3-Amino-1,1,1-trifluoropropan-2-ol, molecular formula is C3H6F3NO, molecular weight is 129.0811, as common compound, the synthetic route is as follows.

A mixture of propyl-(2,6, 8-trichloro-pyrimido [5 ,4-dj pyrimidin-4-yl)-amine(2) (250 mg, 0.85 mmol) and 3-amino-1,1,1-trifluoro-propan-2-ol (221 mg, 1.71 mmol) inTHF (7 mL) was stirred at room temperature for 1 8h. A saturated NaHCO3 solution (30 mL) was added, the resulting suspension was extracted with dichloromethane (3 x 10 mL). The combined organic extracts were washed with brine (30 mL) and dried over solid anhydrous Na2SO4. After filtering, the solvent was removed and the residue was purified by flashcolumn chromatography using gradient elution from PE/EtOAc (3:1) to PE/EtOAc (1:9) to give 3-(2,6-dichloro-8-propylamino-pyrimido[5,4-djpyrimidin-4-ylamino)-1 ,1,1 -trifluoropropan-2-ol (21) (277 mg, 84% yield). ESI-MS (m/z): 385, 387, 389 [M+Hf?.

Statistics shows that 431-38-9 is playing an increasingly important role. we look forward to future research findings about 3-Amino-1,1,1-trifluoropropan-2-ol.

Reference:
Patent; GALLEON PHARMACEUTICALS, INC.; DAX, Scott L.; MENCEL, James Joseph; OZOLA, Vita; SUNA, Edgars; SHUBIN, Kirill; (294 pag.)WO2017/3822; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 86770-74-3, 2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)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, Product Details of 86770-74-3, blongs to alcohols-buliding-blocks compound. Product Details of 86770-74-3

Example 28 Synthesis of Compound 122 To the solution of intermediate carbonate 1B obtained in Example 11 (5.04 mumol, 5 mg) in DCM (7.77 mmol, 0.5 mL) was added 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethan-1-ol (0.050 mmol, 9.75 mg) and Hunig’s base (0.050 mmol, 8.81 muL). The reaction mixture was stirred overnight at rt and the volatiles were removed. The crude material was purified by RP-column chromatography to afford Compound 122 (3.1 mg, 58.8%) as a white solid. Observed ESI HRMS: m/z 1045.6173 [M+H]+. The 1H NMR spectrum of Compound 122 is shown in FIG. 44.

The synthetic route of 86770-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sirenas LLC; MACHERLA, Venkat Rami Reddy; SCHAMMEL, Alexander Wayne; USUI, Ippei; STOUT, Elizabeth Paige; BEVERAGE, Jacob Neal; LEE, Bryan Junn; COHEN, Steven Bruce; (304 pag.)US2017/15710; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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.39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane, molecular formula is C5H10O2, molecular weight is 102.13, as common compound, the synthetic route is as follows.HPLC of Formula: C5H10O2

Into a solution of [l-(hydroxymethyl)cyclopropyl]methanol (9.5 g, 93.02 mmol,) and CC14 (15.57 g, 102.43 mmol) in THF (50 mL) at 0 C was added [bis(dimethylamino)phosphanyl]-dimethylamine (16.70 g, 102.33 mmol). The resulting solution was stirred overnight at room temperature and then quenched by the addition of water. The resulting solution was extracted with DCM and the organic layers combined. The resulting mixture was washed with sat. NaCl and dried over Na2S04 and then concentrated. The residue was purified by chromatography (EtO Ac/pet. ether (1 : 1) to afford 5.2 g (46%) of [1- (chloromethyl)cyclopropyl]methanol as yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane, and friends who are interested can also refer to it.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth Albert; VERNER, Erik; (122 pag.)WO2016/191172; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 2240-88-2, name is 3,3,3-Trifluoropropan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. Safety of 3,3,3-Trifluoropropan-1-ol

ert-butyl 3-hydroxypyrazole-1-carboxylate (2.03 g, 11.02 mmol), 3,3,3-trifluoropropan- 1-ol (approximately 1.320 g, 11.57 mmol), and triphenyl phosphine (approximately 3.189 g, 2.817 mL, 12.16 mmol) were combined in THF (20.40 mL) and the reaction was cooled in an ice bath. To the mixture was added DIAD (approximately 2.507 g, 2.441 mL, 12.40 mmol) dropwise and the reaction was allowed to warm to room temperature for 16 h. The mixture was evaporated and the resulting material was partitioned between ethyl acetate (50 mL) and 1N sodium hydroxide (50 mL). The organics were separated, washed with brine (30 mL), dried over sodium sulfate and evaporated. The crude material was purified by silica gel chromatography eluting with 0-30percent ethyl acetate in hexanes to give tert-butyl 3-(3,3,3-trifluoropropoxy)pyrazole-1- carboxylate (2.0 g, 65percent) ESI-MS m/z calc.280.1035, found 281.1 (M+1)+; Retention time: 0.62 minutes.

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, 2240-88-2, 3,3,3-Trifluoropropan-1-ol.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; ABELA, Alexander, Russell; ALCACIO, Timothy; ANDERSON, Corey; ANGELL, Paul, Timothy; BAEK, Minson; CLEMENS, Jeremy, J.; CLEVELAND, Thomas; FERRIS, Lori, Ann; GROOTENHUIS, Peter Diederik, Jan; GROSS, Raymond, Stanley; GULEVICH, Anton; HADIDA RUAH, Sara, Sabina; HSIA, Clara, Kuang-Ju; HUGHES, Robert, M.; JOSHI, Pramod, Virupax; KANG, Ping; KESHAVARZ-SHOKRI, Ali; KHATUYA, Haripada; KRENITSKY, Paul, John; MCCARTNEY, Jason; MILLER, Mark, Thomas; PARASELLI, Prasuna; PIERRE, Fabrice Jean, Denis; SHI, Yi; SHRESTHA, Muna; SIESEL, David, Andrew; STAVROPOULOS, Kathy; TERMIN, Andreas, P.; UY, Johnny; VAN GOOR, Fredrick, F.; YOUNG, Tomothy, John; ZHOU, Jinglan; (398 pag.)WO2018/107100; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 403-41-8, 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. 403-41-8, name is 1-(4-Fluorophenyl)ethyl Alcohol. A new synthetic method of this compound is introduced below.

General procedure: A round-bottom flask was charged with alcohol (2 mmol), CuOTf (0.1 mmol, 0.05 equiv) (S)-5-(pyrrolidin-2-yl)-1H-tetrazole (0.1 mmol, 0.05 equiv), TEMPO (0.1 mmol, 0.05 equiv), t-BuOK (2 mmol, 1 equiv) and DMF (5 ml). The reaction mixture was stirred at 25 C open to air until the completion of the reaction, as monitored by TLC. The mixture was then diluted with CH2Cl2 (20 ml), washed with water, dried over Na2SO4, and evaporated under vacuum to give the crude product, which was purified by column chromatography to give the pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,403-41-8, 1-(4-Fluorophenyl)ethyl Alcohol, and friends who are interested can also refer to it.

Reference:
Article; Liu, Yangyang; Xie, Aming; Li, Junjian; Xu, Xiao; Dong, Wei; Wang, Boliang; Tetrahedron; vol. 70; 52; (2014); p. 9791 – 9796;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 4728-12-5, (2,2-Dimethyl-1,3-dioxan-5-yl)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, COA of Formula: C7H14O3, blongs to alcohols-buliding-blocks compound. COA of Formula: C7H14O3

To a solution of acetonide (2,2-dimethyl-1,3-dioxan-5-yl)methanol (3.0 g, 20.52 mmol) and tetrabutyl ammonium iodide (7.58 g, 20.52 mmol) in anhydrous THF (100 mL) was added sodium hydride (1.108 g, 27.7 mmol) in 3 portions. The mixture was allowed to stir at room temperature for 1 hour and then treated with benzyl bromide (2.93 ml, 24.63 mmol) over 3 minutes. The mixture was allowed to stir overnight at room temperature (18 hours). The mixture was analyzed by tlc (2:1 hexanes:ethyl acetate) and 1H NMR which showed complete consumption of starting material. The mixture was quenched with saturated ammonium chloride solution (75 mL) and extracted with ethyl acetate (200 mL and 100 mL). Combined organic phases were dried over sodium sulfate and then concentrated to dryness. The crude material was then purified by column chromatography over silica gel eluting with 0-30percent EtOAc/hexanes to obtain MD-02-130 as colorless oil. 1H NMR (400 MHz, chloroform-d) delta 7.35 – 7.24 (m, 5H), 4.50 (s, 2H), 3.96 (dd, J = 12.0, 4.2 Hz, 1H), 3.77 (dd, J = 11.8, 6.4 Hz, 1H), 3.51 (d, J = 6.7 Hz, 2H), 2.04 – 1.97 (m, 1H), 1.41 (s, 3H), 1.38 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4728-12-5, (2,2-Dimethyl-1,3-dioxan-5-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; EMORY UNIVERSITY; LIOTTA, Dennis, C.; PAINTER, George, R.; BLUEMLING, Gregory, R.; DE LA ROSA, Abel; (408 pag.)WO2016/145142; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts