Category: alcohols-buliding-blocks

Application of 2215-78-3, 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.2215-78-3, name is (4-Phenoxyphenyl)methanol, molecular formula is C13H12O2, molecular weight is 200.2332, as common compound, the synthetic route is as follows.

Under an argon atmosphere and dissolved in the above process resulting in 1 4-phenoxyphenylmethanol (122) (300 mg), DPPA (495 mg) in anhydrous DMF (2.7 mL). DBU the (274 mg) was added under ice cooling,the mixture was stirred for 2 hours, the mixture was further stirred for 24 hours at room temperature. Water was added to the reaction mixture, the reaction mixture was extracted with ethyl acetate (30 mL). The organic layer 2N aqueous hydrochloric acid (30 mL), washed with saturated brine (30 mL), dried over anhydrous sodiumsulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash columnchromatography (developing solvent nhexane:ethyl acetate = 50: 1) to give the title compound (103 mg, 30% yield) as acolorless oil.

Statistics shows that 2215-78-3 is playing an increasingly important role. we look forward to future research findings about (4-Phenoxyphenyl)methanol.

Reference:
Patent; Nagoya City University; Miyata, Naoki; Suzuki, Takayoshi; Ota, Yosuke; Ueda, Ryuzo; Ida, Shinsuke; Rie, Masaki; (47 pag.)JP5725475; (2015); B2;,
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Electric Literature of 50919-06-7, 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. 50919-06-7, name is 2-(2-Fluorophenyl)ethanol, molecular formula is C8H9FO, 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.

1.02 g of p-toluensulfonyl chloride (5.35 MM), 1.24 ml of diisopropyl ethylamine (7.13 mmol) and 86mg OF 4- (DIMETHYLAMINO) pyridine (0.71 mmol) were added to the reaction solution (3.57 mmol) containing 500 mg of 2- (2-fluoro-phenyl)- ethanol (3.57 mmol) dissolved in methylene chloride solution with stirring for 6 hrs at 0 C under Ar atmosphere, and then the reaction mixture was stirred for 12hrs at room temperature. The resulting mixture was neutralized with ammonium chloride, extracted with ethyl acetate and washed with saturated NACI solution to separate into an organic layer and water layer. The organic layer was dried over anhydrous MgS04, filtered and concentrated in vacuo. The resultant was purified by Silica gel column chromatography with a solvent mixture mixed with methanol and chloroform (1: 7) as an eluant to give 740 mg of TOLUEN-4-SULFONATE-2- (2-FLUORO-PHENYL)-ETHYL ester (u) (yield : 70%).

According to the analysis of related databases, 50919-06-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Korea Research Institute of Bioscience and Biotechnology; WO2004/101523; (2004); A1;,
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Related Products of 55362-80-6, 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. 55362-80-6, name is 9-Bromononan-1-ol. A new synthetic method of this compound is introduced below.

9-Bromononan-1-ol (3 g. 13.4 mmol) was dissolved in dichloromethane (70 mL, 0.2M) and to this solution were added dimethyl sulfoxide (2.9 mL, 40.3 mmol) and diisopropylethylamine (7.0 mL, 40.3 mmol). The flask was then sealed under nitrogen and cooled to -15 C. Pyridine sulfur trioxide complex (6.4 g, 40.3 mmol) was added in two equal portions over 2 minutes and the resulting mixture was stirred at temperature between -10 C. and -20 C. for 30 minutes. The reaction was then quenched by adding water and the layers were separated. The organic layer was washed with aqueous sodium bisulfate (1M*3) and brine (*1), and then dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound as an amber oil (2.4 g 81% yield). 1H NMR (CDCl3, delta): 9.78 (s, 1H), 3.40 (t, 2H), 2.43 (t, 2H), 1.85 (m, 2H), 1.63 (m, 2H), 1.5-1.25 (m, 8H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55362-80-6, its application will become more common.

Reference:
Patent; Mammen, Mathai; Mischki, Trevor; Hughes, Adam; Ji, Yu-Hua; US2006/35933; (2006); A1;,
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Application of 10488-69-4, Adding some certain compound to certain chemical reactions, such as: 10488-69-4, name is Ethyl 4-chloro-3-hydroxybutanoate,molecular formula is C6H11ClO3, 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 10488-69-4.

Example 7; [72] 41.0 g (1.084 mol) of sodium borohydride and 200 g (1.205 mol, 99.3percent ee) of ethyl (S)-4-chloro-3-hydroxybutyrate were dissolved in 400 g of isopropanol, and 34.7 g (1.084 mol) of methanol was added dropwise at room temperature for 1 hour. After stirring at room temperature for 12 hours, the reaction mixture was cooled below 1O0C. Then, after adding 122 g of 36percent HCl dropwise, the solvent was removed by distillation under reduced pressure below 4O0C. Using 500 mL of methanol, concentration under reduced pressure was performed for 3 times below 4O0C. Stirring was performed after adding 550 mL of isopropanol to the resultant residue. After filtering off solid inorganic materials, 147 g of (S)-4-chloro-l,3-butanediol was obtained as oil (yield = 98percent).

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. 10488-69-4, Ethyl 4-chloro-3-hydroxybutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RSTECH CORPORATION; WO2008/93955; (2008); A1;,
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Electric Literature of 558-42-9, 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.558-42-9, name is 1-Chloro-2-methyl-2-propanol, molecular formula is C4H9ClO, molecular weight is 108.5667, as common compound, the synthetic route is as follows.

To a solution of 2-(3-isopropyl-2-(8-methyl-[l,2,4]?riazolojT,5-a]pyridin-6-yi) lH-indol-5-yl)morpholine, HCI (0.026 g, 0.063 mmol) and l-chloro-2-methylpropan-2-ol (10.28 mg, 0.095 mmol) in DMF (1.00 mL) was added K2CO3 (0.044 g, 0.316 mmol) at room temperature, then stirred at 90 C for 16 h. Crude LCMS showed formation of product, filtered the reaction mass, concentrated the filtrate to afford crude compound, the crude material was purified by preparative LCMS purification using method D2, the fractions containing the product was combined and dried using Genevac centrifugal evaporator to afford l-(2-(3-isopropyl-2-(8-methyl-[l,2,4]triazolo[l,5-a]pyridin-6-yl)-lH- indol-5-yl)morphoIino)-2-methylpropan-2-ol (0.0076 g, 0.017 mmol, 27 % yield) as a pale solid. LCMS retention time 1.923 min [E] MS tn/z: 448.2 [M+H]+; *H NMR (400 MHz, CDJOD) d ppm 8.72 (s, 1 H), 8 47 (s, 1 H), 7.79 (s, 1 1 1 ). 7 67 (s, 1 H), 7.38 (d, J = 8.4 Hz, 1 H), 7.18 (d, J = 8.4 Hz, 1 H), 4.04-3.90 (m, 2 H), 3.80 (s, 1 H), 3.38-3.35 (m, 1 H), 3.13-3.07 (m, 1 H), 3.00-2.94 (m, 1 H), 2.71 (s, 3 H), 2.60-2.51 (m, 1 H), 2.49-2.38 (m, 3 H), 1.52 (dd, J = 7.2, 1.2 Hz, 6 H), 1.26 (s, 3 1 1). 1.25 (s, 3 H).

The chemical industry reduces the impact on the environment during synthesis 558-42-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DYCKMAN, Alaric J.; DODD, Dharmpal S.; MUSSARI, Christopher P.; GILMORE, John L.; HAQUE, Tasir Shamsul; SHERWOOD, Trevor C.; WHITELEY, Brian K.; POSY, Shoshana L.; KUMAR, Sreekantha Ratna; PASUNOORI, Laxman; DURAISAMY, Srinivasan Kunchithapatham; HEGDE, Subramanya; ANUMULA, Rushith Kumar; SRINIVAS, Pitani Veera Venkata; (279 pag.)WO2019/126113; (2019); A1;,
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Application of 15258-73-8, Adding some certain compound to certain chemical reactions, such as: 15258-73-8, name is (2,6-Dichlorophenyl)methanol,molecular formula is C7H6Cl2O, 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 15258-73-8.

A solution of(2,6-dichlorophenyl)methanol (1.07 g, 6.06 mmol) in DMF (15 mL) was treated with NaH (60% in mineral oil; 661 mg, 16.5 mmol) and stirred at rt for 15 mm. The mixture was treated with 2-chloro-7,8-dihydroquinolin-5(6B)-one (1.00 g, 5.51mmol) and stirred at rt for 1.5 h. Chipped ice (5 g) was added and the mixture was extracted twice with EtOAc. The combine organic phases were washed with brine, dried and concentrated. The residue was subjected to column chromatography on silica gel, eluting with EtOAc-hexanes (0-40%), to provide 2-((2,6-dichlorobenzyl)oxy)-7,8- dihydroquinolin-5(6B)-one (1.35 g, 76% yield). LCMS m/z 321.8, 323.8, 325.8 (M+H), HPLC tR 3.71 mm (method B). 1H NMR (400 MHz, CDCl3) delta 8.21 (d, J=8.58 Hz, 1H), 7.37-7.44 (m, 2H), 7.20-7.33 (m, 1H), 6.71 (d, J=8.58 Hz, 1H), 5.69 (s, 2H), 3.09 (t, J=6.16 Hz, 2H), 2.62-2.70 (m, 2H), 2.14-2.28 (m, 2H).

According to the analysis of related databases, 15258-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LIU, Qingjie; DHAR, T.G. Murali; QIN, Lan-ying; XIAO, Hai-Yun; LI, Jianqing; CHERNEY, Robert, J.; (162 pag.)WO2018/71620; (2018); A1;,
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Reference of 2043-47-2 ,Some common heterocyclic compound, 2043-47-2, molecular formula is C6H5F9O, 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.

Example 2In a 5-liter, four-necked glass reactor were placed 3 liters of methylene chloride, 7 g (69 mmol) of triethylamine, 81 g (764 mmol) of sodium carbonate, 100 g (379 mmol) of 3,3,4,4,5,5,6,6,6-nonafluorohexanol and 0.5 g of Sumilizer GM. Thereto was dropwise added 55 g (764 mmol) of acrylic acid. Then, 135 g (765 mmol) of benzenesulfonic acid chloride was added dropwise while the reaction temperature was kept at 40 C. or lower. After the completion of the dropwise addition, stirring was conducted at 30 C. for 2 hours to obtain a reaction mixture. At this point, the conversion was 88% and the selectivity was 99%. 400 ml of water was added to the reaction mixture. Stirring was conducted for 1 hour. Then, the reaction mixture was allowed to stand. An organic layer was separated from an aqueous layer. The organic layer was subjected to distillation under reduced pressure to remove methylene chloride. To the distillation residue obtained was added 2 liters of methylene chloride. There were further added 15 g (148 mmol) of triethylamine and 10 g (139 mmol) of acrylic acid. To the mixture was dropwise added 24 g (136 mmol) of benzenesulfonic acid chloride while the reaction temperature was kept at 40 C. or lower. After the completion of the dropwise addition, stirring was conducted for 2 hours while the temperature of reaction mixture was kept at 30 C. At this point, the conversion was 99% or more and the selectivity was 99%. 250 ml of water was added to the reaction mixture, followed by stirring for 30 minutes. The reaction mixture was allowed to stand. An organic layer was separated from an aqueous layer. The organic layer was washed two times each with 250 ml of water, after which the organic layer was subjected to distillation under reduced pressure to remove the methylene chloride contained therein. To the distillation residue obtained was added 0.5 g of a polymerization inhibitor, Sumilizer GM. The mixture was subjected to distillation under reduced pressure to obtain 101 g (317 mmol, yield: 84%) of 3,3,4,4,5,5,6,6,6-nonafluorohexyl acrylate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2043-47-2, its application will become more common.

Reference:
Patent; TOKUYAMA CORPORATION; DAIKIN INDUSTRIES, LTD.; US2009/23948; (2009); A1;,
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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. 101597-25-5, name is 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, molecular formula is C17H16O3, 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. category: alcohols-buliding-blocks

1.00 g (2.0 mmol) of the naphthol compound (19) and the following propargyl alcohol compound 0.81 g (3.0 mmol) was dissolved in 50 ml of toluene, 0.02 g of camphorsulfonic acid was further added, and the mixture was stirred under heating reflux for 1 hour. After the reaction, the solvent was removed and purification by chromatography on silica gel gave 1.02 g of a white powdery product. The yield was 69%.

With the rapid development of chemical substances, we look forward to future research findings about 101597-25-5.

Reference:
Patent; Tokuyama Corporation; Izumi, Shinobu; Teranishi, Kazuhiro; Daikoku, Yusuke; Sando, Mitsuyoshi; (46 pag.)JP5721544; (2015); B2;,
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Adding a certain compound to certain chemical reactions, such as: 75476-86-7, 6-Bromo-2,3-dihydro-1H-inden-1-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, Formula: C9H9BrO, blongs to alcohols-buliding-blocks compound. Formula: C9H9BrO

To a solution of 6-bromo-2,3-dihydro-1 H-inden-1 -ol (12 g, 56.3 mmol) in 1 ,4-dioxane (100 mL) was added bis(pinacolato)diboron (18.59 g, 73.2 mmol), potassium acetate (13.82 g, 141 mmol) and the mixture was degassed with argon for 20 mm in a sealed tube. PdCI2(dppf) (2.060 g, 2.82 mmol) was added and the reaction mixture was stirred at 90 00 for 2 h. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate wasconcentrated under reduced pressure to afford a crude residue. The crude residue was purified by column chromatography using 20% ethyl acetate in n-hexane as eluent. The eluted fractions were concentrated under reduced pressure to afford the title compound (12 g, 82% yield). 1H NMR (400MHz, ODd3) 5 ppm = 7.88 (s, I H), 7.72 (d, J=7.7 Hz, 1 H), 7.28 (s, 1 H), 5.25 (br t, J=5.8 Hz, 1 H), 3.08 (ddd, J=5.0, 8.4, 16.4 Hz, 1 H), 2.88 – 2.78 (m, 1 H), 2.51 – 2.41 (m, 1 H), 2.01-1.91 (m, 1H), 1.68 (br s, 1H), 1.37-1.27 (m, 12H).

The synthetic route of 75476-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; KERNS, Jeffrey K.; YAN, Hongxing; CALLAHAN, James Francis; HEIGHTMAN, Thomas Daniel; BOEHM, Jeffrey Charles; WOOLFORD, Alison Jo-Anne; (250 pag.)WO2016/203401; (2016); A1;,
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Synthetic Route of 117087-18-0, 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 117087-18-0, name is 2-((Benzyloxy)methyl)propane-1,3-diol. This compound has unique chemical properties. The synthetic route is as follows.

Step 3: ((3-Fluoro-2-(fluoromethyl)propoxy)methyl)benzene To a pre-cooled solution of 2-(benzyloxymethyl)propane-1,3-diol (780 mg, 3.94 mmol) in DCM (20 mL) was added DAST (1.9 g, 11.8 mmol) drop wise at -78 C. The mixture was stirred at 20 C. for 24 hours. The reaction mixture was quenched by sat. NaHCO3 aqueous (10 mL) at -78 C. DCM phase was separated and washed with brine, dried by MgSO4, filtered through a short silica gel pad and then concentrated to give the crude colorless oil (800 mg, 100%). ESI-MS (EI+, m/z): 223 [M+Na]+. 1H NMR (500 MHz, CDCl3) delta 7.37-7.28 (m, 5H), 4.65-4.57 (m, 2H), 4.55-4.48 (m, 4H), 3.57 (d, J=6.2 Hz, 2H), 2.50-2.34 (m, 1H).

According to the analysis of related databases, 117087-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Navitor Pharmaceuticals, Inc.; Fetalvero, Kristina Michelle; Narayan, Sridhar; O’Neill, David John; Saiah, Eddine; Sengupta, Shomit; (93 pag.)US2017/114080; (2017); A1;,
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