Category: alcohols-buliding-blocks

Adding some certain compound to certain chemical reactions, such as: 626-18-6, name is 1,3-Benzenedimethanol, 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 626-18-6. 626-18-6

To a stirred solution of 1, 3-phenylenedimethanol (1) (5 g, 36.496 mmol) in THF (100 mL) was treated with NaH (1.17 g, 29.197 mmol) at 0C to RT for 30 min. Ethyl iodide (2.3 ml, 29.197 mmol) in THF (10 mL) was added to above reaction mixture at OC and stirred at 60 C for 6h under nitrogen atmosphere. The reaction mixture was quenched with ice water and extracted with ethyl acetate (3x100mL). Combined organic layers were washed with brine (2×100 mL) and dried over Na2SO4, evaporated under reduced pressure. Crude residue was purified by Combi-flash chromatography using 20 % ethyl acetate in pet- ether to afford (3-(ethoxy methyl) phenyl) methanol 3 (2.1g, 12.65 mmol, 34 % yield) as a yellowish oily liquid. TLC system: 40 % ethyl acetate in pet-ether – Rf: 0.50; LCMS: m/z = 120.99 (M-46) +

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 626-18-6.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina, C.; LEE, Sam SK; FEESE, Michael, David; (206 pag.)WO2020/23813; (2020); A1;,
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The common heterocyclic compound, 104-29-0, name is 3-(4-Chlorophenoxy)-1,2-propanediol, molecular formula is C9H11ClO3, 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. 104-29-0

General procedure: In a 100 mL stainless steel autoclave, diol (5mmol), catalyst (10 % Pd/C, 0.5 mol %), KI (0.09 mmol), base (1.25 mmol),solvent (10 mL) were added. The autoclave was closed, flushed with nitrogen,pressurized with O2 (33 psi) and CO (167 psi) and reaction mixturewas stirred with a mechanical starrer (520 rpm) at desired temperature forappropriate time period. After completion of reaction, the reactor was thencooled to room temperature, degassed carefully and opened. The reaction mixturewas filtered and the solvent was evaporated under vacuum. The reaction mixturewas analyzed by GC analysis (Perkin-Elmer, Clarus 400) equipped with a flameionization detector (FID) and a capillary column (Elite-1, 30 m ¡Á 0.32 mm ¡Á0.25 mum). Purification of residue was carried out by column chromatography(silica gel 100-200 mesh, petroleum ether/ethyl acetate) to afford thecorresponding products in good to excellent yield. The prepared compounds werecharacterized by 1H NMR (Varian 200 MHz NMR Spectrometer), 13CNMR spectra (50 MHz) and GC-MS (Shimadzu GC-MS QP 2010) (Rtx-17, 30 m ¡Á 25mmID,film thickness 0.25 mum df) (column flow- 2 mL/min, 80 C to 240 C at 10/min.rise.) which were consistent with those reported in the literature

The synthetic route of 104-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chavan, Sujit P.; Bhanage, Bhalchandra M.; Tetrahedron Letters; vol. 55; 6; (2014); p. 1199 – 1202;,
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402-63-1, Adding a certain compound to certain chemical reactions, such as: 402-63-1, 1-(3-Fluorophenyl)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, 402-63-1, blongs to alcohols-buliding-blocks compound.

Step 1: [0747] A solution of 7 (522 mg, 3.0 mmol), 1-(3-fluorophenyl)ethanol (631 mg, 14.5 mmol) and PPh3 (1.18 g, 4.5 mmol) in THF (10 mL) was cooled to 0 C. DIAD (0.87 mL, 4.5 mmol) was added dropwise and the reaction was stirred at room temperature for 3 h. The mixture was concentrated and purified by chromatography (silica gel, 50% ethyl acetate/hexanes) to give 9 (257 mg, 29%) as a white solid: 1H NMR (300 MHz, CDCl3) delta 7.39-7.30 (m, 2H), 7.17 (d, J=2.7 Hz, 1H), 7.11-7.06 (m, 2H), 7.02 (dd, J=9.9, 1.2 Hz, 1H), 6.54 (dd, J=9.9, 1.2 Hz, 1H), 6.36 (q, J=7.2 Hz, 1H), 1.71 (d, J=7.2 Hz, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,402-63-1, its application will become more common.

Reference:
Patent; RVX Therapeutics Inc.; Liu, Shuang; Duffy, Bryan Cordell; Quinn, John Frederick; Jiang, May Xiaowu; Wang, Ruifang; Martin, Gregory Scott; Zhao, He; Molino, Bruce Francis; Young, Peter Ronald; US2014/179648; (2014); A1;,
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2615-15-8, 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. 2615-15-8, name is 3,6,9,12,15-Pentaoxaheptadecane-1,17-diol. This compound has unique chemical properties. The synthetic route is as follows.

Hexaethylene glycol (1.41 g, 5 mmol) Was dissolved in triethylamine (3.5 mL, 25 mmol) And dry Dichloromethane (100 mL), ice bath, Slowly add p-toluenesulfonyl chloride (2.4 g, 15 mmol) Stir at room temperature for 24 hours. TLC (EtOAc) to complete the reaction. Dilute dichloromethane (200 mL) was added, followed by 1 MHC1 , Saturated NaHC03, and saturated NaCl, and the organic phase was dried with anhydrous Na2SO4. After removing Na2S04 by filtration, the organic phase was evaporated to dryness under reduced pressure The mixture was purified by sonar column chromatography (2: l EtOAc / hexanes) to give the product as a colorless oil (2.62 g, 90%)

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 2615-15-8, 3,6,9,12,15-Pentaoxaheptadecane-1,17-diol.

Reference:
Patent; Institute of Microbiology of the Chinese Academy of Sciences (IMCAS); Li, Xuebing; Zhang, Zhenxing; (21 pag.)CN106589014; (2017); A;,
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623-04-1, Adding some certain compound to certain chemical reactions, such as: 623-04-1, name is (4-Aminophenyl)methanol,molecular formula is C7H9NO, 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 623-04-1.

2.15g (17.5mmol) of 4-aminobenzyl alcohol was added to 20mL of 10% HCl aqueous solution at 0C, followed by addition of 1.45g (21.0mmol, 1.2equiv) sodium nitrite dissolved in dry 10mL CH2Cl2. After the mixture was stirred at 0C for 1h, 4mL of sodium azide (1.88g, 28.9mmol) aqueous solution was added drop-wise and stirred overnight. Then, the mixture was quenched with brine and extracted with ethyl acetate (100mL¡Á3). The combined organic layer was dried over anhydrous sodium sulfate and concentrated in vacuum. Finally, the crude product was purified by flash chromatography (petroleum/ethyl acetate=4:1) to give a yellow oil (2.21g, 85%). 1H NMR (400MHz, DMSO): delta=6.95 (d, J=8Hz, 2H), 6.50 (d, J=8Hz, 2H), 4.92 (s, 2H), 4.79 (t, J=8Hz, 1H), 4.28 (d, J=8Hz, 2H) (Fig.S3). 13C NMR (100MHz, DMSO): delta=145.97, 131.13, 128.78, 115.20, 65.16 (Fig.S4)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 623-04-1.

Reference:
Article; Xiang, Kaiqiang; Liu, Yunchang; Li, Changjiang; Tian, Baozhu; Tong, Tianzhong; Zhang, Jinlong; Dyes and Pigments; vol. 123; (2015); p. 78 – 84;,
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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 2807-30-9 as follows., 2807-30-9

General procedure: Method A To a solution of compound 3 (150 mg, o.27 mmol), alcohol (0.81 mmol), and EDCI (576 mg, 3.0 mmol) in CH2Cl2 (30 mL) was added DMAP (122 mg, 1.0 mmol), and the mixture was stirred at room temperature for 12 h. Ethyl acetate (60 mL) was added, and the organic phase was washed three times with water, once with brine, dried, and finally concentrated. There is no need to further purify the residue.

The chemical industry reduces the impact on the environment during synthesis 2807-30-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Liu, Shan Xiang; Jin, Hui Zi; Shan, Lei; Zeng, Hua Wu; Chen, Bing Yang; Sun, Qing Yan; Zhang, Wei Dong; Bioorganic and Medicinal Chemistry Letters; vol. 23; 7; (2013); p. 2207 – 2211;,
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6214-44-4, A common compound: 6214-44-4, name is (4-Ethoxyphenyl)methanol,molecular formula is C9H12O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 5 4-[(4-Ethoxyphenyl)methyl]-1,2-dihydro-5-methyl-3 H -pyrazol-3-one The title compound was prepared in a similar manner to that described in Example 1 using 4-ethoxybenzyl alcohol instead of 4-isopropoxybenzyl alcohol. 1H-NMR (500MHz, DMSO-d6) delta ppm: 1.20-1.35 (3H, m), 1.98 (3H, s), 3.46 (2H, s), 3.85-4.05 (2H, m), 6.70-6.85 (2H, m), 6.95-7.10 (2H, m)

With the rapid development of chemical substances, we look forward to future research findings about 6214-44-4.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP1213296; (2002); A1;,
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100-37-8, Adding a certain compound to certain chemical reactions, such as: 100-37-8, 2-(Diethylamino)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, 100-37-8, blongs to alcohols-buliding-blocks compound.

34.9 g (0.1 mol) of 4- [1- (5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl) ethenyl] benzoic acid (bexarotene; Targretin )) Was dissolved in 300 ml of chloroform.To this reaction mixture was added 20.6 g of N, N’-dicyclohexylcarbodiimide.11.6 g of dimethylaminoethanol was added to the reaction mixture. The mixture was stirred at room temperature for 3 hours. Solids were removed by filtration.The chloroform solution was washed with 5% NaHCO 3 (2 ¡Á 10 0 ml) and water (3 ¡Á 100 ml).The organic solution was dried over anhydrous sodium sulfate.Sodium sulfate was removed by filtration. To this reaction mixture 3.6 g of HCl gas / ether (100 ml) was added with stirring. The solid product was collected by filtration. After drying 40 g of the desired product (85.8%) was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100-37-8, its application will become more common.

Reference:
Patent; YU, CHONGXI; (76 pag.)JP2017/160261; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 431-38-9, 3-Amino-1,1,1-trifluoropropan-2-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, 431-38-9, blongs to alcohols-buliding-blocks compound. 431-38-9

A solution of 100 mg intermediate 32, 75 mg 3-amino-1 ,1 ,1 -trifluoropropan-2-ol, 167 mg HATU and 0.15 mL ethyldiisopropylamine in 5 mL of DMF was stirred at room temperature for 14 hours. Then the reaction was quenched by water, and the mixture was extracted with dichloromethane two times. The combined organic phases were dried over sodium sulfate and evaporated to dryness. The residue was subjected to RP-HPLC (column: X-Bridge C18 5muetaiota 100x30mm, mobile phase: acetonitrile / water (0.1 Vol% formic acid)-gradient)) to yield 90 mg 2-(3,5-difluorophenyl)-6-(4-methylphenyl)-3-oxo-/V-(3,3,3-trifluoro-2-hydroxypropyl)-2,3- dihydropyridazine-4-carboxamide. 1H-NMR (400 MHz, DMSO-d6): delta = 2.37 (s, 3H); 3.47 (ddd, 1 H); 3.74 (ddd, 1 H); 4.17-4.28 (m, 1 H); 6.66 (d, 1 H); 7.34 (d, 2H); 7.47 (tt, 1 H); 7.53-7.58 (m, 2H); 7.87 (d, 2H); 8.64 (s, 1 H); 9.60 (t, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,431-38-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM (DKFZ); SCHMEES, Norbert; GUTCHER, Ilona; IRLBACHER, Horst; BADER, Benjamin; ZHAO, Na; PLATTEN, Michael; (437 pag.)WO2017/202816; (2017); A1;,
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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 431-38-9 as follows., 431-38-9

To a solution of racemic 3-azabicyclo[3.1.0]hexane-1,3-dicarboxylic acid-3-tert-butyl ester (200 mg, 0.88 mmol) in DMF (5 mL), TBTU (339 mg, 1.056 mmol) and TEA (160 muL, 1.14 mmol) are added. Mixture is stirred at room temperature for 10 min, then racemic 3-amino-1,1,1-trifluoro-2-propanol (125 mg, 0.97 mmol) is added and the mixture stirred at room temperature overnight. AcOEt and saturated NaHCO3 are added, the organic phases separated and washed with 10% citric acid and brine. The organic layer is then dried using a phase separator cartridge and evaporated under reduced pressure to furnish the title compound (330 mg, 90% content, 100%), that is used as such. HPLC-MS (Method 2): Rt=0.94 min. MS (ESI pos): m/z=339 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 431-38-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GIOVANNINI, Riccardo; BERTANI, Barbara; FERRARA, Marco; LINGARD, Iain; MAZZAFERRO, Rocco; ROSENBROCK, Holger; US2013/197011; (2013); A1;,
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