Category: alcohols-buliding-blocks

Synthetic Route of 495-76-1, 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.495-76-1, name is Benzo[d][1,3]dioxol-5-ylmethanol, molecular formula is C8H8O3, molecular weight is 152.1473, as common compound, the synthetic route is as follows.

To a solution of the piperonyl alcohol (8) (2.0 g, 13.15 mmol) in anhydrous CH2Cl2 (30 mL), cooled to 0 C and stirred, under an argon atmosphere, freshly distilled PBr3 (3.7 mL, 39.45 mmol), was added dropwise. The resulting solution was kept under stirring at 0 C for a further 20 minutes. After, the ice bath was removed, maintaining the stirring for a further 2 h. The system was cooled again to 0 C and a saturated solution of NaHCO3 (75 mL) was slowly added. Extraction was carried out with ethyl ether (3x 70 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford crude bromide (9). This bromide (used immediately after its preparation) was solubilized with anhydrous acetonitrile (30 mL), treated with triphenylphosphine (3.45 g, 13.15 mmol) and stirred overnight, under reflux. Acetonitrile was removed under reduced pressure and the residue was recrystallized from ethanol to provide (5.21 g) Wittig salt (10) in 83% overall yield. Rf 0.53 (CH2Cl2/MeOH 9:1). mp: 237.2-238.5 C. IR (neat) numax/cm-1: 3018, 1492, 1438, 1246, 1109, 750, 687. 1H NMR (400 MHz, CDCl3) delta 7.80-7.62 (m, 15H), 6.62-6.59 (m, 1H), 6.53 (d, 2H, J=5.5 Hz), 5.87 (s, 2H), 5.28 (d, 2H, J=13.9 Hz). 13C NMR (100 MHz, CDCl3) delta 147.6, 134.9 (d, J=11.5 Hz), 134.2 (d, J=38.6 Hz), 130.0 (d, J=49.7 Hz), 125.3, 119.9 (d, J=36 Hz), 118.0, 117.2, 111.2 (d, J=18.4 Hz), 108.4 (d, J=13.5 Hz), 101.1, 30.4 (d, J=187.4 Hz). HRMS (ESI+) calcd for C26H22BrO2P [M-HBr]+ 397.1352, found 397.1358.

Statistics shows that 495-76-1 is playing an increasingly important role. we look forward to future research findings about Benzo[d][1,3]dioxol-5-ylmethanol.

Reference:
Article; Diaz-Munoz, Gaspar; Isidorio, Raquel Geralda; Miranda, Izabel Luzia; de Souza Dias, Gabriel Nunes; Diaz, Marisa Alves Nogueira; Tetrahedron Letters; vol. 58; 33; (2017); p. 3311 – 3315;,
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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.7589-27-7, name is 2-(4-Fluorophenyl)ethanol, molecular formula is C8H9FO, molecular weight is 140.16, as common compound, the synthetic route is as follows.Recommanded Product: 7589-27-7

To a 50 mL round bottom flask equipped with a stir bar was added 6-chloropyridazin-3-ol (250 mg, 1.9 15 mmol), 2-(4-fluorophenyl)ethanol (268 mg, 1.9 15 mmol), triphenylphosphine (603 mg, 2.298 mmol) and THF (10 mL). To the stirred solution was added DIAD (0.447 mL, 2.298 mmol). The solution had a mild exotherm, then cooled within 5 minutes. The solution was stirred at RT for 2 hrs. The reaction solution was concentrated in vacuo and purified via silica gel chromatography (40 gcolumn, 5-40percent EtOAc:Hex) to afford the semi pure product. The material was further purfied via reverse phase C18 chromatography (55 g column, 20-100percent CH3CN:Water with 0.1percent TFA buffer). The desired fractions were isolated, diluted with sat. sodium bicarbonate solution (25 mL) and EtOAc. The organic layer was washed with brine, collected, dried over MgSO4, and volatiles evaporated to afford the pure product 3-chloro-6-(4-fluorophenethoxy)pyridazine (450 mg, 1.781 mmol, 93 percent yield) as a white solid. 1H NMR (400 MHz, CDC13) 7.22 (dd, J=8.3, 5.4 Hz, 2H), 7.18 (d, J=9.8 Hz, 1H), 7.04 – 6.97 (m, 2H), 6.91 (d, J9.5 Hz, 1H), 4.37 -4.30 (m, 2H), 3.13 – 3.06 (m, 2H). LCMS (M+1) = 253.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7589-27-7, 2-(4-Fluorophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
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Application of 2612-28-4, 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. 2612-28-4, name is 2-Propylpropane-1,3-diol, molecular formula is C6H14O2, 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.

EXAMPLE 5 A mixture of 1.2 g of 2-propylpropane-1,3-diol, 2.59 g of 5-(2-pentyl-5-pyridyl)-2-formyl-thiophene (obtainable by formylation of 5-(2-pentyl-5-pyridyl)-thiophene via a Vilsmeier reaction), 0.01 g of p-toluenesulfonic acid and 15 ml of toluene is boiled for 3 hours, using a water separator, cooled, washed with water and evaporated. 5-(2-Pentyl-5-pyridyl)-2-(trans-5-propyl-1,3-dioxan-2-yl)-thiophene is obtained.

According to the analysis of related databases, 2612-28-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Patent Gesellschaft Mit Beschrankter Huftung; US4659503; (1987); A;,
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Electric Literature of 1261524-75-7, 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.1261524-75-7, name is 3-Bromo-2-chlorobenzyl Alcohol, molecular formula is C7H6BrClO, molecular weight is 221.48, as common compound, the synthetic route is as follows.

To a solution of (3-bromo-2-chlorophenyl)methanol(4.57 g, 20.63 mmol, 1 equiv.) in DCM(200 mL) were added DMF(45.2 mg, 0.62 mmol, 0.03 equiv.) and SOCl2(61.4 g, 516.10 mmol, 25.01 equiv.) dropwise at 0 degrees C under nitrogen atmosphere. The resulting mixture was stirred for 2 days at ambient temperature. The desired product could be detected by LCMS. The mixture was concentrated to get crude product. The crude product was added water(400mL) and extracted with EA (400mLx2). The organic layers was washed with saturated brine (200ml), dried over anhydrous Na2SO4, filtered and concentrated to give desired product. The residue was purified by silica gel column chromatography, eluted with EtOAc / PE (1:50 to 1:40) to afford 1-bromo-2-chloro-3-(chloromethyl)benzene (4.9 g, 98.98%) as a yellow liquid.

The chemical industry reduces the impact on the environment during synthesis 1261524-75-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
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Electric Literature of 748805-85-8, 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 748805-85-8 as follows.

General procedure: A solution of 4-toluene sulfonyl chloride (4.58 g, 1.2 equiv) or methanesulfonyl chloride (1.9 mL, 1.2 equiv) and pyridine (2 mL, 1.3 equiv) in 20 mL CH2Cl2 was added slowly to the solution of compound 11 (0.02 mol) in 40 mL CH2Cl2. The mixture was stirred overnight at room temperature. Then 30 mL diluted HCl solution was added to the reaction mixture, the organic layer was separated using separating funnel. Subequently, the aqueous phase was extracted with 15 mL CH2Cl2 three times, the combined organic layers were washed separately with saturated NaHCO3 (30 mL) and saturated NaCl (30 mL) three times. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography using petroleum ether/EtOAc = 1/1 to give the product 12.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,748805-85-8, its application will become more common.

Reference:
Article; Xu, Changrui; Wu, Zhengxing; Chen, Jianzhong; Xie, Fang; Zhang, Wanbin; Tetrahedron; vol. 73; 14; (2017); p. 1904 – 1910;,
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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 27871-49-4, name is (S)-Methyl 2-hydroxypropanoate. This compound has unique chemical properties. The synthetic route is as follows. Formula: C4H8O3

Under an Ar atmosphere, to a solution of methyl L-lactate (10.0 g, 96.1 mmol) in THF (100.0 mL) were added NEt3 (33.5 mL 240.2 mmol), DMAP (1.17 g, 9.6 mmol) and TBSCl (19.3 g, 128.1 mmol) at 0C, and the mixture was stirred for 24 h at r.t. The reaction mixture was diluted with Et2O, successively washed with 10% HCl aq. and sat. NaHCO3 aq., dried over MgSO4, filtered, and concentrated in vacuo. The resulting oil was purified by column chromatography on silica gel (hexane:AcOEt = 5:1) to afford the TBS ether (S-1) (20.9 g, 95.5 mmol, 99%) as a colorless oil.

With the rapid development of chemical substances, we look forward to future research findings about 27871-49-4.

Reference:
Article; Sugimoto, Kenji; Kobayashi, Yuta; Hori, Ayana; Kondo, Takashi; Toyooka, Naoki; Nemoto, Hideo; Matsuya, Yuji; Tetrahedron; vol. 67; 40; (2011); p. 7681 – 7685;,
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Reference of 5339-85-5, 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. 5339-85-5, name is 2-(2-Aminophenyl)ethanol. A new synthetic method of this compound is introduced below.

General procedure: A test tube (25 mL) wascharged with 2-aminophenethyl alcohol 1? (0.5 mmol, 1 equiv), aldehyde 2?? (0.75mmol, 1.5 equiv), AgOTf (0.025 mmol, 5 mol%), HOTf (0.05 mmol, 10 mol%), and toluene (3 mL) were added. Themixture was stirred at 120 oC in air for 12 hours, thereaction was cooled down to room temperature, the mixture was quenched by sat.aq. NaHCO3, and diluted with 10 mL dichloromethane and washed with10 mL H2O. The aqueous layer was extracted twice withdichloromethane (10 mL) and the combined organic phase was dried over Na2SO4.After evaporation of the solvents, the residue was purified by silica gelchromatography (hexane/AcOEt = 30:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5339-85-5, 2-(2-Aminophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Article; Xu, Xuefeng; Zhang, Xu; Liu, Wenming; Zhao, Qiang; Wang, Zhiqiang; Yu, Lintao; Shi, Fu; Tetrahedron Letters; vol. 56; 24; (2015); p. 3790 – 3792;,
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Synthetic Route of 722-92-9, 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. 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, molecular formula is C9H7F6NO, 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.

2-(4-Ethylamino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol To a solution of 3.0 gm of 2-(4-Amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (Matrix Scientific, Columbia, S.C.) in 30 ml of methylene chloride was added 2.4 ml of triethyl amine, 1.2 ml of acetic anhydride, and 100 mg of dimethylaminopyridine. The mixture was allowed to stir at room temperature for 16 hrs. An additional 2.4 ml of triethyl amine and 1.2 ml of acetic anhydride was added and the mixture was stirred for an additional 6 hrs. The solution was evaporated and purified by column chromatography (1:1 Ethyl Acetate:Hexane) to give 3.1 gm of material that was used in the next step. To this material dissolved in 30 ml of tetrahydrofuran cooled to 0 degrees C. was added 1.6 gm of lithium aluminum hydride. This solution was stirred for 16 hrs and quenched with 1 N sodium hydroxide. This was then extracted with ethyl acetate and dried over anhydrous sodium sulfate. Chromatography gave 2.188 gm of the named product. 1H NMR was consistent with the structure.

According to the analysis of related databases, 722-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Orphagen Pharmaceuticals; Thacher, Scott; Li, Xiaolin; Babine, Robert; Tse, Bruno; US8389739; (2013); B1;,
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Related Products of 869725-53-1, 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 869725-53-1 as follows.

To a vial equipped with a stir bar were added 265 N-(4-fluorophenyl)-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)oxetane-3-carboxamide (I-155; see Ex. 76 for preparation) (500 mg, 1.26 mmol), 671 (2-bromo-5-(trifluoromethyl)phenyl)methanol (320 mg, 1.26 mmol), potassium phosphate tribasic (aq. solution 1M) (2511 mul, 2.51 mmol), (2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1?-biphenyl)[2-(2?-amino-1,1?-biphenyl)]palladium(II) methanesulfonate, and 45 THF (1.26E+04 mul). The vial was purged with nitrogen, sealed, and heated to 40 C. for 1.5 h. After 1.5 h, the crude was washed with EtOAc and sat. NaHCO3. Combined organics were dried over MgSO4, filtered, and concentrated under reduced pressure. The material was dry loaded onto a 120 g column, and the column was run from 100% 6 DCM to 100% 10 EtOAc. The desired product was eluted and fractions were collected and concentrated under reduced pressure. The material was added to a vial, and 70 ACN was slowly added dropwise. Almost immediately, a solid crashed out and there was a resulting liquid. More ACN was added dropwise, swirled, and the solid did not go into solution. The mixture was heated with a heat gun to obtain a uniform solution. The mixture was undisturbed for 3.5 h. After 3.5 h, the sample was moved to the refrigerator for 12 h. After 12 h, the mixture was rinsed with cold (chilled with ice bath) ACN, and the 672 title compound was obtained as a solid. MS (ESI) calc’d for C23H18F4N2O3[M+H]+, 447; found, 447. 1H NMR (600 MHz, DMSO-d6) delta 10.14 (s, 1H), 8.75 (d, J=1.7 Hz, 1H), 8.01 (dd, J=8.2, 2.4 Hz, 1H), 7.97 (s, 1H), 7.78 (d, J=6.9 Hz, 1H), 7.75-7.70 (m, 2H), 7.63 (dd, J=60.7, 8.0 Hz, 2H), 7.25-7.17 (m, 2H), 5.51 (t, J=5.4 Hz, 1H), 5.15 (dd, J=76.2, 6.4 Hz, 4H), 4.52 (d, J=5.4 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,869725-53-1, its application will become more common.

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
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Related Products of 3840-31-1 ,Some common heterocyclic compound, 3840-31-1, molecular formula is C10H14O4, 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: To a 25-mL Schlenk tube equipped with a magnetic stirrer, CuCl (0.05 mol, 5 mol%), DABCO (0.10 mol, 10 mol%), 4-HO-TEMPO (0.05 mmol, 5 mol%) were added. Substrates 1 (1 mmol) and NH3 (aq, 25-28%, 3 mmol, 3.0 equiv) in CH3CN (2 mL) were added subsequently. Then the reaction mixture was stirred at room temperature for 24 h in the presence of an air balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography to afford the corresponding products.

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. 3840-31-1, (3,4,5-Trimethoxyphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hu, Yongke; Chen, Lei; Li, Bindong; Chinese Chemical Letters; vol. 29; 3; (2018); p. 464 – 466;,
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