Month: October 2020

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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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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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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2516-33-8 ,Some common heterocyclic compound, 2516-33-8, molecular formula is C4H8O, 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.

0.49 g (6.82 mmoi) cyclopropane methanol in 10 mL THF are charged with 0.42 g (11.4 mmoi) NaH and the reaction mixture is stirred at r.t. for 20 min. Then 1.00 g (5.68 mmoi) 5-bromo-2-fluoropyridine are added and the mixture is stirred at r.t. over night. The reaction is quenched by the addition of water and extracted with EtOAc. The organic layers are combined, dried over MgS04l filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (MeOH/H20/FA). CgH-ioBrNO (M= 228.1 g/mol) ESI-MS: 228/229 [M+H]+ Rt (HPLC):1.14 min (method C)

According to the analysis of related databases, 2516-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/114578; (2014); A1;,
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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. 624-95-3, name is 3,3-Dimethylbutan-1-ol. A new synthetic method of this compound is introduced below., 624-95-3

[00056] Example I represent a reference oxidation reaction under the conditions analogous to the one (reported in J.Organic Chemistry, 1987, 52, 2559 and J. Organic Chemistry, 1989, 54, 2970), also known as Anelli protocol. [00057] 820 mg of 3,3-Dimethyl-1-butanol (8 mmol) and 14.9 mg MeO-TEMPO (0.08 mmol) are dissolved in toluene (20 cc) in a jacketed glass reaction flask, equipped with a thermocouple, an addition port, a Teflon coated magnetic stir bar and a pH probe. Potassium bromide (45.25 mg, 0.4 mmol) and 1310 mg of NaHCO3 are dissolved in water (21.6 cc) and the aqueous phase is added to the stirred organic fraction at 1000 RPM in the reaction flask. The stirred suspension is cooled to 0 C. and 5.4 g of 12.3% aqueous NaOCl (8.92 mmol) are added via a gas-tight syringe over 5 minutes. The reaction mixture is aged for an additional 30 min and the organic layer sampled for GC assay. The yield of 3,3-dimethylbutyraldehyde is 77% at 30 min and 91% at 60 min reaction time

At the same time, in my other blogs, there are other synthetic methods of this type of compound,624-95-3, 3,3-Dimethylbutan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; The NutraSweet Company; US6825384; (2004); B1;,
Alcohol – Wikipedia,
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Some common heterocyclic compound, 372-30-5, molecular formula is C6H9F3O3, 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.372-30-5

Step 1: synthesis of 4,4,4-trifluoro-3-hydroxybutanamide A solution of ethyl 4,4,4-trifluoro-3-hydroxybutanoate (3.0 g, 16.1 mmol) in MeOH (8 mL) was stirred with aqueous ammonium (16 mL) at room temperature overnight. The mixture was concentrated to afford 4,4,4-trifluoro-3-hydroxybutanamide (2.19 g, yield: 87.6%).

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 372-30-5.

Reference:
Patent; Hoffmann-La Roche Inc.; Feng, Song; Gao, Lu; Hong, Di; Wang, Lisha; Yun, Hongying; Zhao, Shu-Hai; US2015/158879; (2015); A1;,
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612-16-8, 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. 612-16-8, name is (2-Methoxyphenyl)methanol. A new synthetic method of this compound is introduced below.

Step 2: Preparation of 1-(chloromethyl)-2-methoxybenzene To a solution of (2-methoxyphenyl)methanol (1.15 g, 8.32 mmol) and triethylamine (1.24 g, 12.3 mmol, 1.7 mL) in methylene chloride (16 mL) at 0 C. was added dropwise chlorotrimethylsilane (0.939 g, 8.65 mmol). The reaction mixture was stirred in the cooling bath for an additional 30 min after which the cooling bath was removed and stirred at room temperature for 18 h. The reaction mixture was washed with water (10 mL*2), dried over sodium sulfate, filtered and concentrated to give crude 1-(chloromethyl)-2-methoxybenzene (1.36 g, crude) as an orange oil. The material was used directly in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,612-16-8, (2-Methoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Yumanity Therapeutics, Inc.; WRONA, Iwona; TIVITMAHAISOON, Parcharee; TARDIFF, Daniel; PANDYA, Bhaumik; OZBOYA, Kerem; LUCAS, Matthew; BOURDONNEC, Bertrand Le; (259 pag.)US2019/330198; (2019); A1;,
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6214-44-4, 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. 6214-44-4, name is (4-Ethoxyphenyl)methanol, molecular formula is C9H12O2, 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.

General procedure: To a solution of compound 8a (1.08 g, 10 mmol) and Et3N (1.52g, 15 mmol) in anhydrous DCM (100 mL) was added dropwisemethanesulfonyl chloride (1.36 g, 12 mmol) in anhydrous DCM(20 mL). The mixture was stirred for 12 h while being cooled withan ice-water bath. DCM was evaporated under vacuum. The residuewas dissolved in EtOAc (100 mL) and washed with 10% HCl(3 100 mL), saturated NaHCO3 (3 100 mL) and brine (3 100mL), and then dried over MgSO4 overnight. EtOAc was evaporatedto give 11a as yellow oil (1.77 g, yield: 95%). ESI-MS m/z 187.4 [M+H]+. The crude product was used directly in the next reactionwithout further purification.Compounds 11b-11w, 11aa-11ff and 23a-23h were preparedusing the same procedure described above.

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. 6214-44-4, (4-Ethoxyphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cao, Jiangying; Ma, Chunhua; Zang, Jie; Gao, Shuai; Gao, Qianwen; Kong, Xiujie; Yan, Yugang; Liang, Xuewu; Ding, Qin’ge; Zhao, Chunlong; Wang, Binghe; Xu, Wenfang; Zhang, Yingjie; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3145 – 3157;,
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355-80-6, Adding a certain compound to certain chemical reactions, such as: 355-80-6, 2,2,3,3,4,4,5,5-Octafluoro-1-pentanol, 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, 355-80-6, blongs to alcohols-buliding-blocks compound.

General procedure: To a solution of the alcohol 2, 5 (1.48 mmol, 1 equiv) in Et2O/MeCN (3.7:1.23 mL, 3:1 v/v) in 0 C successively imidazole (4.43 g, 3 equiv) and triphenylphosphine (2.22 g, 1.5 equiv) were added. Iodine (2.22 g, 1.5 equiv) was added portionwise over 10-15 min. The solution was kept for a further 20 min at 0 C and then was allowed to warm up to rt overnight. The reaction mixture was diluted with Et2O (12 mLl) and washed with saturated aq Na2S2O3 (10 mL) and brine (2 x 10 mL). The organic layer was dried over Na2SO4 and solvent was removed under vacuum. Column chromatography hexane/EtOAc (1:1 v/v) gave pure product 14, 15. 1-iodo-2,2,3,3,4,4,5,5-octafluoropentane (14). Colorless liquid, yield 0.150 g (36%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,355-80-6, its application will become more common.

Reference:
Article; Tomaszewska, Joanna; Koroniak-Szejn, Katarzyna; Koroniak, Henryk; Arkivoc; vol. 2017; 2; (2016); p. 421 – 432;,
Alcohol – Wikipedia,
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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 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane. This compound has unique chemical properties. The synthetic route is as follows. 39590-81-3

1,1-Cyclopropanedimethanol (1.02 g; 10 mmol) is dissolved in dimethylformamide (20 ml; dried over a molecular sieve) and, after addition of potassium tert-butylate (1.14 g, 10 mmol), the mixture is stirred at room temperature for 1 hour. The reaction mixture is then cooled to 0-5 C. and a solution of rmethyl iodide (0.63 ml; 10 mmol) in dimethylformamide (5 ml; dried over a molecular sieve) is then added dropwise. After stirring at this temperature for 50 minutes, the reaction mixture is poured on to a mixture of a saturated aqueous NH4Cl solution (100 ml) and diethyl ether (400 ml), while stirring. After separation of the phases, the aqueous phase is re-extracted with diethyl ether (400 ml) and the combined organic phases are washed with a saturated aqueous sodium chloride solution (2*100 ml), dried over magnesium sulphate, filtered with suction and concentrated. The crude product obtained is chromatographed over silica gel (50 g) with diethyl ether. Yield: 493 mg (39%) (1-methoxymethyl-cyclopropyl)-methanol as a pale yellow oil. NMR (1H, 250 MHz in CDCl3) in ppm: 0.5-0.6 (multiplet, 4H); 3.37 (multiplet, 5H); 3.54 (s,2H)

Statistics shows that 39590-81-3 is playing an increasingly important role. we look forward to future research findings about 1,1-Bis(Hydroxymethyl)cyclopropane.

Reference:
Patent; Basilea Pharmaceutica AG; US6821980; (2004); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts