Month: May 2021

Electric Literature of 2568-33-4, Adding some certain compound to certain chemical reactions, such as: 2568-33-4, name is 3-Methylbutane-1,3-diol,molecular formula is C5H12O2, 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 2568-33-4.

The 3 – methyl – 1, 3 butanediol (14 A) (5.0 g, 48 mmol) dissolved in dichloromethane (100 ml) in, add triethylamine (9.7 g, 96 mmol), 0 C slow […] carboxylic acid isopropyl ester (8.8 g, 72 mmol), transfusion reaction at room temperature for 3 hours. The reaction solution by adding water (100 ml) washing, for liquid phase after the saturated salt water (100 ml × 1) washing, drying with anhydrous sodium sulfate, filtered, the filtrate is concentrated under reduced pressure, the residue with silica gel column chromatography (ethyl acetate/petroleum ether (v/v)=1/10 – 1/1) separating and purifying, to obtain the title compound (3 – hydroxy -3 – methyl – butyl) isopropyl carbonate (14 B), colorless oily matter (4.5 g, yield 49%).

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. 2568-33-4, 3-Methylbutane-1,3-diol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Qiu Guanpeng; Wei Yonggang; Lu Yonghua; Huang Qingping; Liao Pengfei; (41 pag.)CN107382870; (2017); A;,
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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. 3597-91-9, name is [1,1′-Biphenyl]-4-ylmethanol. A new synthetic method of this compound is introduced below., COA of Formula: C13H12O

General procedure: p-Nitrobenzyl alcohol (0.25 g, 1.63 mmol) was dissolved in anhydrous CH2Cl2 under N2. Triethylamine (0.227 mL, 1.63 mmol) was added and the resulting solution was cooled to 0 C. S2Cl2 (65.3 muL, 0.82 mmol) was added dropwise over 20 min. The solution was stirred at 0 C for 2 h before being allowed to equilibrate to room temperature for 3 h. The reaction was quenched with dH20, washed with 2 × 20 mL aliquots of brine. The aqueous phase was extracted with CH2Cl2 (2 × 10 mL), and the combined organic was dried over MgSO4, filtered, and concentrated under reduced pressure. Column chromatography with a 2.5:1 ratio of hexanes:ethyl acetate afforded:

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, 3597-91-9, [1,1′-Biphenyl]-4-ylmethanol.

Reference:
Article; Stoutenburg, Eric G.; Palermo, Anne E.; Priefer, Ronny; Thermochimica Acta; vol. 551; (2013); p. 99 – 103;,
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Reference of 6153-05-5 , The common heterocyclic compound, 6153-05-5, name is (Z)-3-Methylpent-2-en-4-yn-1-ol, molecular formula is C6H8O, 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.

(Z)-3-Mehylpent-2-en-4-yn-1-ol(side chain) (68 mg, 0.70 mmol) in dry THF (3.5 mL) was cooled to ?80 °C unde ran atmosphere of Ar. n-Butyllithium(0.90 mL, 1.58 M) was then added slowly. After being stirred for 30 min at ?80°C, a solution of the 6 (64 mg, 0.35mmol) in dry THF (0.5 mL) was added to the stirred mixture. The reaction mixture was stirred for a further 15 min at ?80 °C and then the ice bath was removed. The reaction mixture was stirred at room temperature for 90 min. After quenching with sat. NH4Cl solution (100 mL), it was extracted withEtOAc (15 mL × 3). The organic layer was washed with brine, dried over Na2SO4,and concentrated in vacuo. The residual oil was purified by silica gel chromatography with 55percent EtOAc in hexane to obtain 7 (58 mg, 59percent) as a yellow oil. 1H NMR (270 MHz, CDCl3): deltaH 1.12 (3H, s,H3-8? or 9?), 1.17 (3H, s, H3-8? or 9?), 1.88 (3H, d, J=1.0, H3-6), 1.94 (2H, s, H2-5?),2.08 (1H, s, -OH), 3.96 (4H, br s, -OCH2CH2O-), 4.29(2H, d, J=5.3 Hz, H2-1),5.60 (1H, d, J=9.9 Hz, H-2? or 3?),5.87 (1H, td, J=5.3 and 1.0 Hz, H-2),5.89 (1H, d, J=9.9 Hz, H-2? or 3?); 13CNMR (68 MHz, CDCl3): deltaC 22.6, 23.0, 25.6, 39.2, 43.7,61.6, 64.3, 64.5, 72.0, 77.2, 84.1, 104.7, 120.5, 127.0, 134.0, 136.1. HRMS (m/z): [M+Na]+ calcd. for C16H22O4Na,301.1416; found, 301.1415.

The synthetic route of 6153-05-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Takeuchi, Jun; Ohnishi, Toshiyuki; Okamoto, Masanori; Todoroki, Yasushi; Bioorganic and Medicinal Chemistry Letters; vol. 25; 17; (2015); p. 3507 – 3510;,
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Related Products of 349-95-1, 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.349-95-1, name is (4-(Trifluoromethyl)phenyl)methanol, molecular formula is C8H7F3O, molecular weight is 176.14, as common compound, the synthetic route is as follows.

4-methyl-benzenesulfonamide (171mg, 1mmol), catalyst A (8.3mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), 4- trifluoromethylbenzyl alcohol ( 211mg, 1.2mmol) and water (1ml) were successively added to the reaction flask 25mlSchlenk.After the reaction mixture was reacted at 120 15 hours, cooled to room temperature.Heavy precipitate precipitated, water was removed by filtration, the filter cake was washed with water three times to give the title compound, yield: 84%

Statistics shows that 349-95-1 is playing an increasingly important role. we look forward to future research findings about (4-(Trifluoromethyl)phenyl)methanol.

Reference:
Patent; Nanjing University of Science & Technology; Li, Feng; Qu, panpan; Sun, chunlou; Ma, Juan; (17 pag.)CN104418678; (2016); B;,
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Electric Literature of 6995-79-5 ,Some common heterocyclic compound, 6995-79-5, molecular formula is C6H12O2, 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 solution of (1 r,4r)-cyclohexane-1 ,4-diol (3 g, 25.8 mmol) and (0875) imidazole(2.64 g, 38.7 mmol) in DMF (30 mL) was added TBS-CI (4.28 g, 28.4 mmol) The mixture was stirred at rt for 3 day. The mixture was diluted with water (150 mL), extracted with DCM three times. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuum (high vacuum at 70C to remove most DMF ) to afford a light oil. The residue was loaded purified by CombiFlash, eluted with methanol in DCM (0-5%, 30 min). Collected the desired fraction and concentrated in vacuum to afford the title compound (6 g, 80%) as colorless syrup. 1 H NMR (400 MHz, DMSO-d6) delta 3.72 – 3.35 (m, 2H), 1 .80 – 1 .58 (m, 4H), 1 .37 – 1 .06 (m, 4H), 0.82 (s, 9H), 0.00 (s, 6H).

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. 6995-79-5, trans-Cyclohexane-1,4-diol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; DU-CUNY, Lei; XIAO, Qitao; XUN, Guoliang; ZHENG, Qiangang; (204 pag.)WO2018/234978; (2018); A1;,
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Reference of 928-51-8, 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 928-51-8, name is 4-Chlorobutan-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of DMSO (10ml) taken in a round bottom flask was added KOH (2equiv) and the solution was stirred at room temperature for 15min. The indole derivative 2 or 20 (1equiv) was then added and the mixture was further stirred for 1h, after which 4-chlorobutan-1-ol or 3-chloropropan-1-ol (1.5equiv) was added dropwise to the reaction mixture. The reaction was monitored by TLC to completion within 5h. The reaction mixture was then quenched by adding water and was extracted with ethyl acetate. Evaporation of the solvent under reduced pressure followed by column chromatography gave the required N-alkylated compounds, 3/13/21. 4.3.1 1-(4-Hydroxybutyl)-1H-indole-3-carbaldehyde (3) White solid (85%); mp 12 75-77 C.

According to the analysis of related databases, 928-51-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Naik, Prajakta N.; Khan, Ayesha; Kusurkar, Radhika S.; Tetrahedron; vol. 69; 50; (2013); p. 10733 – 10738;,
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Related Products of 4415-82-1 ,Some common heterocyclic compound, 4415-82-1, molecular formula is C5H10O, 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.

A solution of 11.1 ml (116.1 mmol) of oxalyl chloride in 50 ml of abs. dichloromethane was cooled to -78 C., and a solution of 16.5 ml (232.2 mmol) of DMSO in 50 ml of abs. dichloromethane was added dropwise, keeping the temperature below -50 C. After 5 min, a solution of 10.0 g (116.1 mmol) of cyclobutanemethanol in 20 ml of abs. dichloromethane was added dropwise. After a further 15 min of stirring at -78 C., 80.9 ml (580.5 mmol) of triethylamine were added. After 5 min, cooling was removed and the mixture was slowly warmed to RT, and the reaction mixture was then added to water. The mixture was saturated with sodium chloride and the separated organic phase was washed twice with saturated sodium chloride solution, three times with 1 N hydrochloric acid and three times with pH buffer solution, dried over sodium sulphate and concentrated under reduced pressure (500 mbar). This gave 6.28 g of cyclobutanecarbaldehyde as a crude product which was directly reacted further.

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. 4415-82-1, Cyclobutylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HAHN, Michael; LAMPE, Thomas; STASCH, Johannes-Peter; SCHLEMMER, Karl-Heinz; WUNDER, Frank; LI, Volkhart Min-Jian; BECKER, Eva-Maria; STOLL, Friederike; KNORR, Andreas; WOLTERING, Elisabeth; US2013/79412; (2013); 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. 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, the common compound, a new synthetic route is introduced below. Formula: C9H7F6NO

Phenylacetyl chloride (940 mg, 6.10 mmol) was added to a solution of methyl 3- amino-2-thiophenecarboxylate (500 mg, 3.18 mmol) and triethylamine (640 mg, 6.30 mmol) in tetrahydrofuran (10 ml), and the resulting mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium hydrogencarbonate solution, water and saturated aqueous sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue obtained was purified by preparative thin layer chromatography to yield pale yellow oil (290 mg, yield: 33percent). This product was dissolved in tetrahydrofuran (3 ml) and methanol (5 ml), and 10percent sodium hydroxide solution (5 ml) was added. The resulting mixture was stirred at room temperature for 36 hours. The reaction mixture was acidified with 1N-hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to yield a pale purple solid. This product and triphenyl phosphite (282 mg, 0.91 mmol) was dissolved in pyridine (5 ml), and the mixture was stirred at 100°C for 2 hours. 2- (4-AMINOPHENYL)-1, 1, 1, 3,3, 3-hexafluoro-2-propanol (235 mg, 0.91 mmol) was added to the reaction solution, and the mixture was further stirred at 120°C for 4 hours. At the end of this time, the reaction mixture was concentrated in vacuo, and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with 1N-hydrochloric acid and saturated aqueous sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue obtained was purified by silica gel column chromatography to yield a pale yellow solid. This product was further purified by preparative thin layer chromatography to yield the title compound as a colorless powder (57 mg, yield: 13percent). mp 257-258°C. IR (KBR) : VMAX 3248, 3088, 1660, 1551, 1268,1213, 1187,937, 708 CRN 1. H-NMR (400MHZ, DMSO-d6) : 8 8.89, (1H, s), 7.68 (2H, d, J = 8.6 Hz), 7.61 (1H, d, J = 5.5 Hz), 7.39 (1H, d, J = 5.5 Hz), 7.33 (2H, d, J = 8.6 Hz), 7.19-7. 08 (3H, m), 6.75 (2H, d, J = 6.3 Hz), 3.82 (2H, s). FABMS (m/z): 485 ([M+H] +).

The synthetic route of 722-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANKYO COMPANY, LIMITED; X-CEPTOR THERAPEUTICS, INC.; WO2003/106435; (2003); A1;,
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Synthetic Route of 929-06-6, 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. 929-06-6, name is 2-(2-Aminoethoxy)ethanol, molecular formula is C4H11NO2, 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.

To a 500mL three-necked flask were added compound BG04 3.7g (1. 0eq), (Boc)2O 15.5g (2.0 eq), a mixed solution of methanol:triethylamine (9:1) 200ml, stirred and warmed to reflux, and reacted for 1h. After the completion of the reaction under the monitor of TLC, methanol triethylamine was evaporated off, and dissolved in water. Dichloromethane was extracted for 3 times. The organic layers were combined and washed once with water, dried over anhydrous sodium sulfate, and concentrated to give 4.8g BG05 as an oil.

According to the analysis of related databases, 929-06-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bright Gene Bio-Medical Technology Co., Ltd.; YUAN, Jiandong; HUANG, Yangqing; SONG, Yunsong; YUAN, Fang; (69 pag.)EP3321279; (2018); A1;,
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Electric Literature of 149965-40-2, 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. 149965-40-2, name is (5-Bromo-2-chlorophenyl)methanol. A new synthetic method of this compound is introduced below.

Step 2: ((5 -bromo-2-chlorobenzyl)oxy)(tert-butyl)dimethylsilane A solution of (5 -bromo-2- chlorophenyl)methanol (3.80 g, 17.2 mmol), tert-butylchlorodimethylsilane (2.84 g, 18.9 mmol), and 1H-imidazole (2.34 g, 34.3 mmol) in DMF (30 mL) was maintained with stirring at 10 C for 16 hours. Then the reaction mixture was poured into diethyl ether (10 mL) and washed three times with 5% LiC1 (15 mL). The organic layer was separated, dried over sodium sulfate, filtered, taken toa residue under reduced pressure. The residue was purified by column chromatography (Si02, petroleum ether= 100%) to give the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,149965-40-2, (5-Bromo-2-chlorophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CHEN, Helen; COLLETTI, Steven, L.; DEMONG, Duane; GUO, Yan; MILLER, Michael; NAIR, Anilkumar; PLUMMER, Christopher, W.; XIAO, Dong; YANG, De-Yi; (289 pag.)WO2016/22742; (2016); A1;,
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