Category: alcohols-buliding-blocks

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. 13330-96-6, name is 4-(Dimethylamino)butan-1-ol, molecular formula is C6H15NO, 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 4-(Dimethylamino)butan-1-ol

General procedure: To a solution of 6-substituted pyridazinone 9 (0.5 mmol) in DMF (10 mL) was added Cs2CO3 (0.55 mmol). An appropriately substituted nitro benzyl chloride (0.52 mmol) was added and the resulting mixture was stirred at 40-50 C for 3 h, the solvent was removed under reduced pressure and the residue was dissolved in EtOAc (30 mL), which was then washed with brine (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product, 2-nitrobenzyl-6-substituted-pyridazin-3(2H)-one (10), was used in the next step without further purification. To a solution of 10 in 95 % ethanol (50 mL) was added acetic acid (10 mmol) followed by slow addition of iron powder (2 mmol). The resulting mixture was stirred for 5 h at 100 C. The mixture was then filtered through celite and the filter cake was washed with 95 % ethanol (3 × 15 mL). The combined ethanol filtrates were evaporated in vacuo and the residue was re-dissolved in ethyl acetate (30 mL). The organic layer was washed with brine (3 × 10 mL) and 2 M NaOH (10 mL) sequentially. The organic layer was dried over anhydrous Na2SO4, evaporated in vacuo to afford 2-aminobenzyl-6-substituted-pyridazin-3(2H)-one (11) as a yellow solid, which was used without further purification. To a stirred solution of 11 and triphosgene (1 mmol) in dry dichloromethane (5 mL) was added triethylamine (2 mmol) under nitrogen atmosphere. A solution of the corresponding alcohol (1 mmol) in dichloromethane (5 mL) was added 5-10 min later and the mixture was stirred at room temperature overnight, diluted with dichloromethane (15 mL) and washed with water (3 × 20 mL). The organic phases were separated, combined, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by using column chromatography to afford the corresponding product.

With the rapid development of chemical substances, we look forward to future research findings about 13330-96-6.

Reference:
Article; Xing, Weiqiang; Ai, Jing; Jin, Shiyu; Shi, Zhangxing; Peng, Xia; Wang, Lang; Ji, Yinchun; Lu, Dong; Liu, Yang; Geng, Meiyu; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 302 – 312;,
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Reference of 83647-43-2 , The common heterocyclic compound, 83647-43-2, name is (3-Bromo-2-methylphenyl)methanol, molecular formula is C8H9BrO, 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.

To a fiask charged with (3-bromo-2- methylphenyl)methanol (6.0 g, 30 mmol) was added a lM TFA solution of thallium trifluoroacetate (16.2 g, 29.8 mmol). The mixture was stirred at RT oyernight. Analysis by TLC showed no starting material remaining. The solyent was remoyed under yacuum, and the residuewas pumped under high yacuum for 30 min to ensure complete remoyal of TFA. To the residue was then added palladium(II) chloride (529 mg, 2.98 mmol), lithium chloride (2.53 g, 59.7 mmol), magnesium oxide (2.41 g, 59.7 mmol), and MeOH (150 mL). The reaction was flushed with CO twice, and kept under CO at room temperature. Analysis by LC showed a big product spot within 2 hours. To this solution was added ethyl acetate to precipitate the salts. The blaeksolution was filtered through a CELITE pad, washed with EtOAc, adsorbed onto silica and purified by silica gel chromatography to afford title compound. 1H-NMR (500 MHz, CDC13)ppm 7.71 (d, J= 8.0 Hz, 1H), 7.58 (d, J= 8.0 Hz, 1H), 5.25 (s, 2H), 2.37 (s, 3H).

The synthetic route of 83647-43-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DE JESUS, Reynalda, Keh; DING, Fa-xiang; DONG, Shuzhi; FRIE, Jessica; GU, Xin; JIANG, Jinlong; SHAHRIPOUR, Aurash; PIO, Barbara; TANG, Haifeng; WALSH, Shawn; WO2014/126944; (2014); A2;,
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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. 3597-91-9, name is [1,1′-Biphenyl]-4-ylmethanol, the common compound, a new synthetic route is introduced below. Formula: C13H12O

In the glove box,Mn(CO)5Br (0.005 mmol),[(E)-2-(2-(1-(2-pyridyl)ethylidene)-indenyl)pyridine] (0.006 mmol),Add 1.0 mL of toluene, stir for two hours, add 2-methylquinoline 4 (2 mmol),2 g (1 mmol), after reacting at 135 C for 48 hours, the reaction was stopped and the solvent was evaporated., column chromatography ethyl acetate / petroleum ether (1:10),The trans-disubstituted olefin derivative 3ag. The product was a white solid with a yield of 92%.

The synthetic route of 3597-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Qingdao University of Science and Technology; Zhang Chunyan; (19 pag.)CN108250153; (2018); A;,
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Application of 41175-50-2, 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. 41175-50-2, name is 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol. A new synthetic method of this compound is introduced below.

Hydroxyjulolidine (3.7 g, 19.3 mmol) and diphenyl malonate (4.1 g, 15.9 mmol) were added into anhydrous toluene (10 mL). The mixture was heated to reflux for 4 h, and compound 2 was obtained by filtration as a straw yellow solid (3.6 g, 88%): mp 268-270C; NMR (400 MHz, DMSO): delta (ppm) 1 1.73 (s, 1H), 7.15 (s, 1H), 5.21 (s, 1H), 3.24-3.20 (m, 4H), 2.70 (s, 4H), 1.91-1.83 (m, 4H); 13C NMR (100 MHz, DMSO): delta (ppm) 166.5, 162.8, 151.0, 146.0, 119.8, 117.3, 105.3, 103.1, 85.8, 49.2, 48.7, 26.9, 21.0, 20.1, 20.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,41175-50-2, its application will become more common.

Reference:
Patent; MICHIGAN TECHNOLOGICAL UNIVERSITY; BI, Lanrong; WO2014/63033; (2014); 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. 456-47-3, name is 3-Fluorobenzyl alcohol, molecular formula is C7H7FO, 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. SDS of cas: 456-47-3

General procedure: GeneralProcedure for the preparation of 2-Phenyl-1H-benzoimidazole (3aa): A 25mL over-dried Schlenk tube was charged with 2-nitroaniline (41.4 mg, 0.3 mmol),benzyl alcohol (97.2 mg, 0.90 mmol) and Pd(dppf)Cl2 (12.2 mg, 0.015mmol). The tube was purged with nitrogen three times. Toluene (1 mL) was addedto the sealed reaction vessel by syringe. The reaction mixture was stirred in apreheated oil bath at 160 oC for 24 h. After cooling to roomtemperature, the reaction mixture was then concentrated in vacuo, and theresidue was purified by column chromatography (silica gel, petroleumether/ ethyl acetate = 4:1) to give 3aa as a pale yellow solid (56.5 mg, 97%).

With the rapid development of chemical substances, we look forward to future research findings about 456-47-3.

Reference:
Article; Li, Xiaotong; Hu, Renhe; Tong, Yao; Pan, Qiang; Miao, Dazhuang; Han, Shiqing; Tetrahedron Letters; vol. 57; 41; (2016); p. 4645 – 4649;,
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Synthetic Route of 6329-73-3, 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. 6329-73-3, name is 1-(Benzo[d][1,3]dioxol-5-yl)ethanol, molecular formula is C9H10O3, 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 stirred solution of alcohol (1 equiv) in dry DCM (10 to 20 mL), thionyl chloride (1 .7 to 3 equiv) was added slowly at 0 C. The reaction mixture was warmed to rt and was refluxed for 1 h. The reaction mixture was concentrated under vacuum and the resulting residue was diluted with DCM (20 to 50 mL). The DCM layer was washed with water (5 to 10 mL), brine solution (5 to 10 mL), dried over anhydrous Na2SO4 and concentrated under vacuum to give chloro compound.

According to the analysis of related databases, 6329-73-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASCENEURON SA; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; (243 pag.)WO2016/30443; (2016); A1;,
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Electric Literature of 455-01-6, 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. 455-01-6, name is 2-(3-(Trifluoromethyl)phenyl)ethanol. A new synthetic method of this compound is introduced below.

Reference Example 19-1 [3-(Trifluoromethyl)phenyl]acetaldehyde To a solution of 3-(trifluoromethyl)phenethyl alcohol (2.00 g) in chloroform (50.0 mL), Dess-Martin periodinane (4.70 g) was added under cooling with ice. After being brought to room temperature, the reaction mixture was stirred for an hour. Subsequently, a saturated aqueous solution of sodium hydrogencarbonate (25.0 mL) and a saturated aqueous solution of sodium thiosulfate (25.0 mL) were added and the mixture was vigorously stirred for an hour. After phase separation, the organic layer was dried over anhydrous magnesium sulfate, the desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 98:2-85:15) to give the titled compound as a pale yellow oil (1.19 g). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 3.79 (s, 2 H) 7.36 – 7.62 (m, 4 H) 9.77 – 9.81 (m, 1 H). MS ESI/APCI Dual nega: 187[M-H]-.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,455-01-6, 2-(3-(Trifluoromethyl)phenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; TAKAYAMA, Tetsuo; SHIBATA, Tsuyoshi; SHIOZAWA, Fumiyasu; KAWABE, Kenichi; SHIMIZU, Yuki; HAMADA, Makoto; HIRATATE, Akira; TAKAHASHI, Masato; USHIYAMA, Fumihito; OI, Takahiro; SHIRASAKI, Yoshihisa; MATSUDA, Daisuke; KOIZUMI, Chie; KATO, Sota; EP2881384; (2015); A1;,
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Electric Literature of 3279-95-6, 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. 3279-95-6, name is 2-(Aminooxy)ethanol, molecular formula is C2H7NO2, 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.

Starting from intermediate 1.i (0.103 g; 0.2 mmol) and 2-aminooxyethanol (0.017 g; 0.221 mmol), the solutionwas stirred for th. The reaction mixture was directly purified by prep-HPLC (Method 1) to afford the titlecompound (0.084 g, 86% yield) as a white amorphous solid.MS1 (ESI, m/z): 485.1 [M+H*] for CigH2aN4O7So; tr = 0.65 min.

According to the analysis of related databases, 3279-95-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; DIETHELM, Stefan; MATHIEU, Gaelle; PANCHAUD, Philippe; SURIVET, Jean-Philippe; TIDTEN-LUKSCH, Naomi; (123 pag.)WO2019/38362; (2019); 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. 1562-00-1, name is Sodium isethionate, molecular formula is C2H5NaO4S, 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. SDS of cas: 1562-00-1

Approximately 1.7 g of Compound A was added to a bottle and dissolved in 34 mL of acetone, concentration of 50 mg/mL. 400 pL (20 mg of freebase) of the stock solution was then dispensed into 84 vials and the acetone allowed to evaporate. 1M stock solutions of each counterion were prepared in either THF, ethanol or water, where appropriate as outlined in Table 27. L-aspartic acid was added as neat counterion due to low solubility. 1.05 equivalents of each counterion was added at room temperature and observations made. 2-hydroxy ethanesulfonic acid was supplied as a sodium salt and had 1.05 equivalents of HC1 added after counterion addition. All samples were then temperature cycled using the following procedure: a) Heat to 40 C, hold for 1 hour; b) Cooled to room temperature, hold for 3 hours; c) Heat to 40 C, hold for 1 hour; and d) Samples were held at 5 C overnight.All samples displaying solutions had the lids removed from the vials and were allowed to evaporate at ambient temperature. Samples with solid material had the mother liquor removed and the solids analyzed by XRPD. The mother liquor was transferred to a new sample vial and stored at 5 C to allow for further precipitation. The analyzed solids on the XRPD plate were exposed to 40 C/75 % RH conditions for 6 hours before analysis by XRPD. Table 27. Solvents Used to make Acid Stock Solutions

With the rapid development of chemical substances, we look forward to future research findings about 1562-00-1.

Reference:
Patent; ALDEYRA THERAPEUTICS, INC.; MACHATHA, Stephen, Gitu; LOUGHREY, Jonathan, James; MCLACHLAN, Hannah, Ruth; SNEDDON, Gregor; (194 pag.)WO2020/33344; (2020); A1;,
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Reference of 3513-81-3, 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 3513-81-3 as follows.

2-METHYLENE-1, 3-propanediol (2.20 g, 25.0 MM) was stirred in dichloromethane (20 ML) and cooled to 0 °C. A 1 N solution of diethylzinc in hexanes (3.40 g, 27.5 MM) was added followed by a solution OF 4-BROMO-3-FLUORO-N-HYDROXYBENZENECARBOXIMIDOYL chloride (6.30 g, 25.0 MM) in dichloromethane (40 mL). The reaction was allowed to warm to room temperature and was complete after four hours. The solution was diluted with ammonium chloride and extracted using dichloromethane. The organic layer was dried (magnesium sulfate), filtered and concentrated to give the desired product as a yellow solid (4.72 g). MS (ESP : 305 (MH+) for CLLHLLBREINO3 300 MHz NMR (DMSO-D 6 : 3.29 (s, 2H); 3.55 (s, 2H); 3.57 (s, 2H) ; 5.10 (t, 2H); 7.52 (d, 1H); 7.68 (d, 1H); 7.86 (t, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3513-81-3, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/48392; (2004); A1;,
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