Tag: M.W=100-200

Electric Literature of 5339-85-5 , The common heterocyclic compound, 5339-85-5, name is 2-(2-Aminophenyl)ethanol, molecular formula is C8H11NO, 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.

2-(Aminophenyl)ethanol(11, 2.4 g, 20 mmol, 1.0 equiv) was dissolved in CH2Cl2(40 mL, abs.) and cooled to 0 C. Pyridiniumchlorochromate(PCC, 13, 6.5 g, 30 mmol, 1.5 equiv) was added in small portions.The mixture was kept at 0 C for 1 h and then stirred for 4 h at room temperature. Silica was added to the mixture and the solvent was evaporated. Purification was performed by distillation. Yield 71.9%. 1H NMR (500 MHz, DMSO) d 6.60(s, 2H), 6.66 (d, J = 8.1 Hz, 1H), 6.73-6.77 (m, 1H), 7.27-7.32(m, 1H), 7.45 (d, J = 8.2, 1H), 9.89 (s, 1H). 13C NMR (126 MHz,DMSO) d 115.5, 116.2, 118.4, 134.9, 135.5, 149.3, 193.1.C7H7NO. MS (ESI+): m/z 122.6 (4.5, (M+H)+), 144.6 (100,(M+Na)+). (agrees with28)

The synthetic route of 5339-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Merk, Daniel; Gabler, Matthias; Gomez, Roberto Carrasco; Flesch, Daniel; Hanke, Thomas; Kaiser, Astrid; Lamers, Christina; Werz, Oliver; Schneider, Gisbert; Schubert-Zsilavecz, Manfred; Bioorganic and Medicinal Chemistry; vol. 22; 8; (2014); p. 2447 – 2460;,
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Adding a certain compound to certain chemical reactions, such as: 10488-69-4, Ethyl 4-chloro-3-hydroxybutanoate, 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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

Example 21 : pH profiles of enzymatic and nonenzymatic test reactions of ethyl 4-chloro- 3-hydroxybutyrate with cyanide Aqueous solutions containing 25 MG/ML sodium cyanide were prepared at pH 5.0, 6.0, 7.0, 7.5, 8. 0, 8. 5, and 9.0 by the addition of 85percent phosphoric acid while monitoring with pH meter. 5 mL of each solution was charged to a SEPARATE 20 ML screw cap vial. Halohydrin dehalogenase SEQ ID NO: 38 (20 mg) was added to each vial, followed by ethyl (S)-4-chloro-3-hydroxybutyrate (50 mg, 0.30 mmoles). For nonenzymatic reactions experiments, the procedure was identical with the exception that the enzyme was omitted. The vials were capped and heated in an oil bath at 55 °C for 3 hrs, then removed and cooled to room temperature. A 0.4 mL sample of each reaction mixture was extracted with 1 mL butyl acetate and the extracts were analyzed by gas chromatography. The analyzed amounts of substrate and products in each vial are given in Table I, and graphed vs. pH in Figure 1. IN BOTH, CHLOROHYDRIN means ethyl (S)-4-chloro-3- hydroxybutyrate, cyanohydrin means ethyl (R)-4-CYANO-3-HYDROXYBUTYRATE, and crotonate means ethyl 4-hydroxycrotonate. In the Table, ND means not detected. Table I : Millimoles CHLOROHYDRIN, cyanohydrin and crotonate by-product analyzed in test reactions with and without HALOHYDHN dehalogenase. See Example 21 without halohydrin dehalogenase with halohydrin dehalogenase mmol mmol mmol mmol mmol mmol PH chlorohydrin cyanohydrin crotonate chlorohydrin cyanohydrin crotonate 5.0 0. 33 ND ND 0. 27 ND ND 6. 0 0. 29 ND ND 0. 07 0. 20 ND 7. 0 0. 30 ND ND 0. 01 0. 28 ND 7.5 0.3 ND ND 0. 004 0. 30 ND 8. 0 0.30 0.01 ND 0.002 0.29 ND 8. 5 0. 21 0. 05 0. 001 0. 001 0. 24 ND 9. 0 0.11 0.10 0.002 0.001 0.21 ND The pHs of the final test reaction mixtures were remeasured. For the mixtures including halohydrin dehalogenase with initial pHs of 7 or above (being the mixtures in which near complete conversion of the CHLOROHYDRIN to the cyanohydrin occurred, the final mixture pHs were 0.4 to 0.6 pH units below the initial pHs. The other mixtures showed much lesser changes in pH from their initial values. These data show that under these reaction conditions and time, no measurable nonenzymatic reaction of the ethyl 4-CHLORO-3-HYDROXYBUTYRATE with cyanide occurred at any tested pH less than 8. At pH 8 and above, increasing nonenzymatic reaction with cyanide to form ethyl 4-cyano-3-hydroxybutyrate occurred with increasing pH and was accompanied by increasing formation of ethyl 4-hydroxycrotonate by-product. In contrast, the enzymatic reaction with halohydrin dehalogenase occurred at all the tested pH’s greater than 5 and with no detectable formation of ethyl 4-hydroxycrotonate at any tested pH. Additionally, for both enzymatic and nonenzymatic test reactions at pH greater than 8, the mole total of the GC- analyzed products decreased from the initial 0.30 MMOLES provided (as ethyl 4-chloro-3- hydroxybutyrate reactant) indicating the increasing formation of non-analyzable by-products with increasing pH greater than 8. It was separately established that the ester group of the reactant and product are increasingly HYDROLYZED to carboxylic acid groups at pHs greater than 8 and that the resulting carboxylic acids are not extracted in to the extracts of reaction mixture samples that are analyzed by GC. See Example 22.

The synthetic route of 10488-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CODEXIS, INC.; WO2005/18579; (2005); A2;,
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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. 4277-34-3, name is Cyclooct-4-enol, molecular formula is C8H14O, 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. Quality Control of Cyclooct-4-enol

Synthesis of Cer-TCO (FIG. 7) (0139) Cis-1,5-cyclooctadiene 1 was converted to cyclooctene monoepoxide 2 with m-CPBA (Clark, et al., 2010, J. Am. Chem. Soc. 132:3405-3412). The monoepoxide was reduced with LiAlH4 to the alcohol 3 (Clark, et al., 2010, J. Am. Chem. Soc. 132:3405-3412). Cis-cyclooctenol 3 was isomerized to trans-cyclooctenol 4 according to Royzen, et al., 2008, J. Am. Chem. Soc. 130:3760-3761. From TCO 4 the corresponding p-nitrophenol carbonate 5 was prepared (Liu, et al., 2012, J. Am. Chem. Soc. 134:792-795).

With the rapid development of chemical substances, we look forward to future research findings about 4277-34-3.

Reference:
Patent; Yale University; ERDMANN, Roman; SHRADER, Alanna Schepartz; TOOMRE, Derek; (34 pag.)US2016/115180; (2016); 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. 101-32-6, name is 2,2-(Benzylimino)diethanol. A new synthetic method of this compound is introduced below., Recommanded Product: 2,2-(Benzylimino)diethanol

2-[Benzyl-(2-hydroxyethyl)amino]ethanol (XIX); 16.9 ml (142 mmol) of benzyl bromide were added to a stirred solution of 15.0 g (142 mmol) of diethanolamine and 39.4 g (285 mmol) of potassium carbonate in 200 ml of acetone, and the solution was then heated under reflux for 3 h. The cooled reaction mixture was filtered and concentrated in vacuo. 100 ml of water were added, and the aqueous mixture was extracted with chloroform (3×60). The combined organic phases were washed with water and saturated NaCI solution and dried over magnesium sulfate, and the solvent was removed in vacuo. Yield: 26.9 g (96%) of colorless oil The reaction product was converted into the hydrochloride by dissolving the residue in 70 ml of 5N ethereal HCI and removing the solvent in vacuo. The residue was then coevaporated with toluene twice. Yield: 31.7 g (99%) of colorless oil 1H-NMR (DMSOd6): 2.51-2.59 (m, 2H), 3.41-3.48 (m, 4H), 3.65 (s, 2H), 4.34 (bs, 2H), 7.16-7.36 (m, 5H). MS (API-ES,pos) m/z = 196 [M+H]+

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, 101-32-6, 2,2-(Benzylimino)diethanol.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2008/25736; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 870-72-4, Hydroxymethanesulfonic Acid Sodium Salt, 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, Safety of Hydroxymethanesulfonic Acid Sodium Salt, blongs to alcohols-buliding-blocks compound. Safety of Hydroxymethanesulfonic Acid Sodium Salt

Intermediate M 18 (10 g, 67.9 mmol) was dissolved in tetrahydrofuran:Water = 1: 1 solution (20 ml)Sodium hydroxymethanesulfonate (9.56 g, 71.3 mmol)And the mixture was heated under reflux at 70 C. for 4 hours. After the reaction solution was cooled to room temperature, it was filtered to obtain Intermediate M19(16.2 g, yield 91%) was obtained.

The synthetic route of 870-72-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIKIN INDUSTRIES LIMITED; KARUBE, DAISUKE; KISHIMOTO, MASAYUKI; CHAKI, TAKEHIRO; KOMATSU, YUZO; (34 pag.)JP2017/82096; (2017); A;,
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Electric Literature of 134575-13-6, Adding some certain compound to certain chemical reactions, such as: 134575-13-6, name is exo-3-Azabicyclo[3.1.0]hexan-6-ylmethanol,molecular formula is C6H11NO, 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 134575-13-6.

Step A (1alpha,5alpha,6alpha)-3-(tert-Butoxycarbonyl)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane A solution of di-tert-butyl dicarbonate (967 mg, 4.42 mmol) in CH2Cl2 (3.0 mL) was added to a stirred solution of (1alpha,5alpha,6alpha)-6-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane (456 mg, 4.02 mmol, for preparation see K. E. Brighty and M. J. Castaldi, Synlett, 1996, 1097-1099) in CH2Cl2 (7.0 mL) at RT. After 15 h, the solution was partitioned between 2 N aq. HCl (50 mL) and EtOAc (50 mL). The organic layer was washed with saturated aq. NaHCO3 (50 mL) and saturated aq. NaCl (50 mL). The aqueous layers were extracted in succession with EtOAc (2*50 mL). The organic layers were dried (Na2SO4), decanted, and evaporated. The crude product was purified by flash column chromatography on silica gel, eluding with 80:20 v/v to 0:100 hexane/EtOAc to give the title compound as a colorless syrup. For the title compound: 1H NMR (500 MHz, CDCl3) delta 3.60 (d, J=11, 2H), 3.53 (d, J=6, 2H), 3.36 (d, J=11, 2H), 1.44 (s, 11H), 0.96 (tt, J=6, 3, 1H); ESI-MS 158.1 (M+H-56); HPLC A: 2.09 min.

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. 134575-13-6, exo-3-Azabicyclo[3.1.0]hexan-6-ylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hale, Jeffrey J.; Lynch, Christopher L.; Caldwell, Charles G.; Willoughby, Christopher A.; Kim, Dooseop; Shen, Dong-Ming; Mills, Sander G.; Chapman, Kevin T.; Chen, Liya; Gentry, Amy; MacCoss, Malcolm; Konteatis, Zenon D.; US2002/94989; (2002); A1;,
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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. 52059-53-7, name is 2-(3-Fluorophenyl)ethanol, the common compound, a new synthetic route is introduced below. HPLC of Formula: C8H9FO

General procedure: To a neat mixture of 3-(3-((6-fluoropyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2-amine (Intermediate IV, 50 mg, 0.19 mmol) and (3-fluorophenyl)methanol (187 mg, 1.48 mmol) was added potassium tert-butoxide (1M in THF, 1.85 mL, 1.85 mmol) and the mixture was stirred for 30 min. The mixture was transferred to a silica gel samplet and purified by column chromatography (SiO2, hexane/ethyl acetate). Combined fractions containing the product were concentrated under reduced pressure. Residue was dissolved in acetonitrile (5 mL) and water (10 mL), frozen and lyophilized to yield 3-(3-((6-((3-fluorobenzyl)oxy)pyridin-3-yl)methyl)isoxazol-5-yl)pyridin-2-amine (45 mg, 0.12 mmol, 65%) as a white solid.

The synthetic route of 52059-53-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Trzoss, Michael; Covel, Jonathan A.; Kapoor, Mili; Moloney, Molly K.; Soltow, Quinlyn A.; Webb, Peter J.; Shaw, Karen Joy; Bioorganic and Medicinal Chemistry Letters; vol. 29; 23; (2019);,
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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.1777-82-8, name is (2,4-Dichlorophenyl)methanol, molecular formula is C7H6Cl2O, molecular weight is 177.03, as common compound, the synthetic route is as follows.Formula: C7H6Cl2O

General procedure: A mixture of alcohol or phenol (1 mmol), DHP (1.2-1.4 mmol), and MNPs-PSA (5 mg, 0.95 mol%) was stirred at room temperature in dry CH2Cl2 (2 mL), and the progress of the reaction was monitored by TLC. After completion of the reaction, catalyst was separated by an external magnet and washed with CH2Cl2. Then, the pure product was isolated by passing of the reaction mixture through a short column using n-hexane and ethyl acetate (9:1) as eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1777-82-8, (2,4-Dichlorophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Rostami, Amin; Tahmasbi, Bahman; Abedi, Fatemeh; Research on Chemical Intermediates; vol. 42; 4; (2016); p. 3689 – 3701;,
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Synthetic Route of 3973-18-0, 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. 3973-18-0, name is Propynol ethoxylate. A new synthetic method of this compound is introduced below.

Preparation of 2-(prop-2-yn-l-yloxy)ethyl trifluoromethanesulfonate 4. To a solution of 2-(prop-2-yn-l-yloxy)ethanol (3) (1.50 g, 15.0 mmol) in (( (20 mL) was added 2,6-lutidine (2.44 mL, 21.0 mmol) followed by trifluoromethanesulfonic anhydride (3.15 mL, 18.7 mmol) at -50 C under argon atmosphere. The mixture was stirred at -10 C for 2 h. It was then partitioned between 50% EtOAc in hexanes (150 mL) and brine (15 mL). The organic layer was separated, washed with brine (15 mL) and dried over anhydrous MgS04. The insoluble was filtered and the filtrate was evaporated in vacuo. The crude material was purified by silica gel column chromatography (silica gel: 50 g, solvent 10% EtOAc in hexanes (500 mL)). The desired fractions were combined and evaporated in vacuo to give the titled compound (2.49 g, 72%) as a dark brown oil. This material was used for the next reaction without further purification. [0313] ln NMR (400 MHz, CDC13) delta 4.64-4.66 (2H, m), 4.22^1.25 (2H, m), 3.85-3.88 (2H, m), 2.48-2.49 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3973-18-0, Propynol ethoxylate, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SHOKAT, Kevan; OKANIWA, Masanori; (209 pag.)WO2016/40806; (2016); A1;,
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Application of 4254-29-9, 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. 4254-29-9, name is 2,3-Dihydro-1H-inden-2-ol, molecular formula is C9H10O, 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 25 mL, one-necked, round-bottomed flask was placed Fe(acac)3 (36 mg, 0.10 mmol, 5 mol %), benzyl alcohol (216 mg, 208 muL, 2 mmol), and Na2CO3 (10.6 mg, 0.10 mmol, 5 mol %) in 10 mL heptane at room temperature under nitrogen atmosphere. A solution of methyl benzoate (272 mg, 256 muL, 2 mmol) in heptane (10 mL) was added via syringe. The resulting mixture was heated to reflux with the removal of the methanol by Dean-Stark apparatus and the reaction progress was monitored by TLC, 1H NMR spectroscopy, and GC analysis until completion of the reaction (6 h). The reaction mixture was then gradually cooled to room temperature and quenched with saturated aqueous NH4Cl solution (5 mL), then extracted with 20 mL ethyl acetate. The combined organic layer was dried (anhydrous MgSO4), filtered, and evaporated to give a crude product that was purified by column chromatography on silica gel (hexane/AcOEt=50/1) to provide the pure benzyl benzoate product 412 mg, 97% yield.

According to the analysis of related databases, 4254-29-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Weng, Shiue-Shien; Ke, Chih-Shueh; Chen, Fong-Kuang; Lyu, You-Fu; Lin, Guan-Ying; Tetrahedron; vol. 67; 9; (2011); p. 1640 – 1648;,
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