Category: alcohols-buliding-blocks

Electric Literature of 402-63-1, 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. 402-63-1, name is 1-(3-Fluorophenyl)ethanol. A new synthetic method of this compound is introduced below.

Example 100 1-(3-Fluorophenyl)ethyl N-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}carbamate 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (99 mg) was added to toluene/triethylamine = 10/1 (10 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (150 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 3-fluoro-alpha-methylbenzyl alcohol (70 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (60 mg, yield 36%). 1H-NMR (CDCl3, 400 MHz): 8.75 (1H, s), 7.98 (1H, bs), 8.47 (1H, bs), 6.48 – 7.60 (9H, m), 5.82 – 5.90 (1H, m), 4.13 (3H, s), 4.08 (3H, s), 1.58 (3H, d, J = 6.6 Hz) Mass spectrometry value (ESI-MS, m/z): 464 (M++1)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,402-63-1, 1-(3-Fluorophenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1243582; (2002); A1;,
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Application of 111-90-0, 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 111-90-0, name is Diethylene Glycol Monoethyl Ether. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of DCM, diethylene glycol mono ethyl ether (21.0 ml_, 150 mmol), and triethylamine (34.7 ml_, 250 mmol) under a nitrogen atmosphere at -78 0C was added dropwise bromo acetyl bromide (17.2 ml_, 200 mmol). After stirring at -78 0C for 3 h, the reaction mixture was allowed to warm up to -20 0C and quenched by addition of water (50 ml_). The organic phase was washed with distilled water (3 x 50 ml_), saturated ammonium chloride (3 x 50 ml_), saturated sodium bicarbonate (3 x 50 ml_) and brine (2 x 50 ml_). The organic phase was then dried over magnesium sulfate, filtered and solvents removed via rotary evaporation to yield a crude product in 87 % yield. This crude product was distilled (bp 105 – 115 0C) to give a colourless liquid at RT in 71 % yield.

According to the analysis of related databases, 111-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DUBLIN CITY UNIVERSITY; WO2009/24607; (2009); A1;,
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Related Products of 395-23-3, 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. 395-23-3, name is Phenyl(4-(trifluoromethyl)phenyl)methanol. A new synthetic method of this compound is introduced below.

Example 171: l-(4-Fluorophenyl)-3-(phenyl(4-(trifluoromethyl)phi methyl)ureaStep 1. Phenyl(4-(trifluoromethyl)phenyl)methanoneA solution of 4-(trifluoromethyl)benzhydrol (1.836 g, 7.3 mmol) in anhydrous DCM (65 mL) was treated with manganese(IV) oxide (<5 micron, activated) (5.7 g, 66 mmol). The resulting suspension was stirred at rt for 12 days. The catalyst was removed by filtration through a Celite brand filter agent pad. The filtrate was concentrated, and the resulting solid was dried under high vacuum to afford the title compound as a white solid. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,395-23-3, its application will become more common. Reference:
Patent; AMGEN INC.; BROWN, James; CHEN, Jian J.; GORE, Vijay Keshav; HARRIED, Scott; HORNE, Daniel B.; KALLER, Matthew R.; LIU, Qingyian; MONENSCHEIN, Holger; NGUYEN, Thomas T.; NISHIMURA, Nobuko; ZHONG, Wenge; WO2012/177896; (2012); A1;,
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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.3068-00-6, name is 1,2,4-Butanetriol, molecular formula is C4H10O3, molecular weight is 106.1204, as common compound, the synthetic route is as follows.name: 1,2,4-Butanetriol

Synthesis of 2,2-Dilinoleyl-4-(2-hydroxyethyl)[1,3]-dioxolane (II) A mixture of dilinoleyl ketone (I, previously prepared as described in Example 1, 527 mg, 1.0 mmol), 1,3,4-butanetriol (technical grade, ca. 90%, 236 mg, 2 mmol) and pyridinium p-toluenesulfonate (50 mg, 0.2 mmol) in 50 mL of toluene was refluxed under nitrogen overnight with a Dean-Stark tube to remove water. The resulting mixture was cooled to room temperature. The organic phase was washed with water (2*30 mL), brine (50 mL), and dried over anhydrous Na2SO4. Evaporation of the solvent resulted in a yellowish oily residual (0.6 g). The crude product was purified by column chromatography on silica gel (230-400 mesh, 100 mL) with dichloromethane as eluent. This afforded 0.5 g of pure II as colourless oil. 1H NMR (400 MHz, CDCl3) delta: 5.25-5.48 (8H, m, 4*CH=CH), 4.18-4.22 (1H, m, OCH), 4.08 (1H, dd, OCH), 3.82 (2H, t, OCH2), 3.53 (1H, t, OCH), 2.78 (4H, t, 2*C=C-CH2-C=C), 2.06 (8H, q, 4* allylic CH2), 1.77-1.93 (2H, m, CH2), 1.52-1.68 (4H, m, 2*CH2), 1.22-1.45 (32H, m), 0.86-0.94 (6H, t, 2*CH3) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3068-00-6, 1,2,4-Butanetriol, and friends who are interested can also refer to it.

Reference:
Patent; Protiva Biotherapeutics, Inc.; US2011/195127; (2011); A1;,
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Synthetic Route of 63478-76-2, 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.63478-76-2, name is 6-Heptyn-1-ol, molecular formula is C7H12O, molecular weight is 112.1696, as common compound, the synthetic route is as follows.

A solution of Dess-Martin-periodinane (5.09 g, 12.0 mmol, 2.0 equiv) in dry DCM (27 mL) was cooled to 0 C, 6-heptyn-1-ol (673 mg, 6.00 mmol, 1.0 equiv) in DCM (3 mL) was added and the mixture was stirred at 23 C for 5 h. DCM (5 mL) was added, the mixture was washed with sat. aq. Na2S2O3-sol. (30 mL), 1 M NaOH (30 mL), and sat. aq. NaCl (30 mL). The aq. phase was extracted with DCM (90 mL), the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The residue was purified on silica gel (n-pentane/Et2O, 9:1) to yield the title compound as a colourless oil (337 mg, 3.06 mmol, 51%).

Statistics shows that 63478-76-2 is playing an increasingly important role. we look forward to future research findings about 6-Heptyn-1-ol.

Reference:
Article; Rode, Katharina; Palomba, Martina; Ortgies, Stefan; Rieger, Rene; Breder, Alexander; Synthesis; vol. 50; 19; (2018); p. 3875 – 3885;,
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Application of 5299-60-5 ,Some common heterocyclic compound, 5299-60-5, molecular formula is C8H16O3, 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.

General procedure: To a stirred solution of esters 2a-2j (70 mmol) in MeOH (30 mL) cooled in an ice-water bath was added dropwise 80% aqueous hydrazine hydrate (6.26 g, 100 mmol). The resulting solution was stirred at room temperature (2a-2b or 2d-2j), or reflux (2c), until the completion of reaction as indicated by TLC analysis (typically within 5 h). The reaction mixture was evaporated on a rotary evaporator to give a residue, which was purified by column chromatography through a short silica gel column to yield 3a-3k after trituration with n-hexane if possible.

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. 5299-60-5, Ethyl 6-hydroxyhexanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tian, He; Liu, Wei; Zhou, Zhixing; Shang, Qian; Liu, Yuqiang; Xie, Yafei; Liu, Changying; Xu, Weiren; Tang, Lida; Wang, Jianwu; Zhao, Guilong; Molecules; vol. 21; 11; (2016);,
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Application of 627-18-9, Adding some certain compound to certain chemical reactions, such as: 627-18-9, name is 3-Bromopropan-1-ol,molecular formula is C3H7BrO, 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 627-18-9.

Bromopropanol (1.38g, 0.01mol) and sodium azide (0.975g, 0.015mol) were dissolved in N,N-dimethylformamide (DMF) and reacted under nitrogen for 90 h at 12 C. . After the reaction is completed, the solution is cooled to room temperature, diluted with a certain amount of water, and the aqueous layer is washed with a large amount of diethyl ether. The ether solution is collected and dried overnight with anhydrous NaS04. The crude product after filtration is purified by column chromatography. The residual DMF organic solvent is removed, and the developing solvent is ethyl acetate: petroleum ether = 1:5, and the obtained colorless liquid is the product azidopropanol.The yield was 0.873 g and the yield was 86.4%. Azido hexanol (0.69 g, 89.2%) and azido undecanol (0.98 g, 91.7%) were prepared by the same procedure.

According to the analysis of related databases, 627-18-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Jiao Tong University; Zhu Xinyuan; Zhang Jun; Fan Wenbin; Zhang Chuan; Xue Feng; Tong Gangsheng; (15 pag.)CN109912528; (2019); A;,
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Application of 109-83-1 ,Some common heterocyclic compound, 109-83-1, molecular formula is C3H9NO, 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 4: Preparation of the compound of formula; (a) Alkylating agent; A mixture of 21.5g 2-hydroxyethyl-methylamine are neutralized with hydrochloric acid and evaporated to dryness.The salt is suspended in chloroform and cooled with stirring to O0C and then 41.Og thionyl chloride are added in small amounts maintaining the temperature at O0C by external cooling. After completion of the addition the reaction is finished by heating to reflux and autgassing the mixture.The solution is evaporated to dryness; the 2-chloroethyl-methylamine used as chlorohydrate in the following step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109-83-1, its application will become more common.

Reference:
Patent; CIBA SPECIALTY CHEMICALS HOLDING INC.; WO2007/25889; (2007); A2;,
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Related Products of 2002-24-6, 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. 2002-24-6, name is 2-Aminoethanol hydrochloride. A new synthetic method of this compound is introduced below.

9-(2′-Hydroxyethylamino)-4-methoxy-1-nitroacridine 4-Methoxy-1-nitro-9-phenoxyacridine (0.346 g) is dissolved in phenol (30 g), ethanolamine hydrochloride (0.12 g) is added and the mixture is heated at 80 C. for 1.5 hour. The reaction mixture is cooled to room temperature, diluted with dry ether (20 ml), slowly poured into dry ether (200 ml) and acidified with ethereal solution of hydrogen chloride. The resulting precipitate is filtered off, washed several times with ether and crystallized from absolute ethanol-ether (5:1) to give 9-(2′-hydroxyethylamino)-4-methoxy-1-nitroacridine monohydrochloride as yellow crystals (0.27 g, 77% yield), m.p. 210-212 C. (decomp.) 1H NMR (for a free base) (d6DMSO): delta10.18 (s, 1 H, NH), 7.78 (d, 1 H, J=7.8 Hz, H-8), 7.67 (d, 1 H, J=8.3 Hz, H-5), 7.47 (t, 1 H, J=7.8 Hz, H-6), 7.36 (d, 1 H, J=8.8 Hz), 7.10 (m, 2 H, H-3, H-7), 4.31 (t, 1 H, J=5.4 Hz, OH), 3.70 (t, 2 H, J=6.4 Hz, H-1′), 3.64 (q, 2 H, J=6.3 Hz, H-2′).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2002-24-6, its application will become more common.

Reference:
Patent; Tiwari, Raj; Miller, Daniel G.; Konopa, Jerzy Kazimierz; Wysocka-Skrzela, Barbara; US2002/37831; (2002); A1;,
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Synthetic Route of 722-92-9, Adding some certain compound to certain chemical reactions, such as: 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol,molecular formula is C9H7F6NO, 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 722-92-9.

The product from step 1 (500 mg, 1.9 [MMOL)] and ethyl acetoacetate [(0. 27] mL, 2.1 [MMOL)] were combined and dissolved in methanol (10 mL) at ambient temperature. To this solution was added glacial acetic acid (0.13 mL, 2.1 [MMOL)] followed by sodium [CYANOBOROHYDRIDE] (194 mg, 3.1 [MMOL).] After stirring 18 h, the solution was [CONCENTRATED IN VACUO] and the resultant oil dissolved in ethyl acetate. The organics were washed with brine, dried over [MGS04,] and concentrated. Purification by reverse phase HPLC using a gradient elution of 60: 40 H20/TFA : CH3CN to 0: 100 H20/TFA : CH3CN at 254 nm afforded the title compound as a white solid (440 mg, [61 percent)] : mp = 103 [¡ãC.] H NMR [(CDC . S) 8] 7.43 (d, 2H), 6.64 (d, 2H), 4.07 (q, 2H), 3.90 (m, 1H), 3.43 (br s, 1 H), 2.58 (dd, 1 H), 2.41 (dd, [1 H),] 1.23 (d, 3H), 1.17 (t, 3H). MS (ES+) m/z 374 [(MH+).] [ANAL. CALC.] for C15H17NO3F6: C, 48.26 ; H, 4.59 ; N, 3.75. Found: C, 47.95 ; H, 4.45 ; N, 3.58.

According to the analysis of related databases, 722-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PHARMACIA CORPORATION; WO2003/99769; (2003); A1;,
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