Category: alcohols-buliding-blocks

Synthetic Route of 1072-52-2, Adding some certain compound to certain chemical reactions, such as: 1072-52-2, name is 2-(Aziridin-1-yl)ethanol,molecular formula is C4H9NO, 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 1072-52-2.

Example 16 (Table 1, entry 8 and Scheme 11): Preparation of methyl 3-[N-(2- iodoethyl)-N- [2- [(methylsulfonyl)oxy] ethyl] amino] -2,6-dinitrobenzoate (27c); A stirred5 solution of methyl 3-chloro-2,6-dinitrobenzoate (25) (140 mg, 0.54 mmol) in DMF (1.5 mL) at» , room temperature was treated with NaI (405 mg, 2.7 mmol) for 5 min, then cooled to 0 0C and treated with aziridineethanol (0.15 mL, 1.87 mmol). The mixture was stirred at 30 0C for 16 h, then diluted with IN aqueous AcOH (15 mL) and extracted with EtOAc (2×15 mL). The combined organic phases were washed with water (2x), dried, and concentrated under10 reduced pressure. The residue was chromatographed on silica gel, eluting with EtOAc/petroleum ether (1:1). The middle fractions were combined and concentrated to small volume, then hexane was added to precipitate methyl 3-[N-(2-hydroxyethyl)-N-2- (iodoethyl)amino]-2,6-dinitrobenzoate (26c) (138 mg, 58%) as a yellow gum: 1H NMR [(CDj)2SO] delta 8.24 (d, J = 9.7 Hz, 1 H), 7.59 (d, J = 9.7 Hz, 1 H), 4.79 (tj = 5.2 Hz, 1 H), 3.8715 (s, 3 H), 3.71 (t, / = 7.2 Hz, 2 H), 3.53 (q, / = 5.1 Hz, 2 H), 3.40-3.33 (m, 4 H). HRMS(FAB) calcd. for C12H15IN3O7 [MH+] m/* 439.9955; found 439.9960.

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. 1072-52-2, 2-(Aziridin-1-yl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AUCKLAND UNISERVICES LIMITED; WO2008/30112; (2008); A1;,
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Electric Literature of 4654-39-1, 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 4654-39-1, name is 2-(4-Bromophenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

Dissolve 31.56g of iodine, 33.91g of triphenylphosphine and 22.35mg of imidazole in anhydrous dichloromethane (100mL), After 30 minutes in an ice bath, 20 g of p-bromobenzyl alcohol was dissolved in anhydrous dichloromethane (50 mL) and quickly added dropwise to the reaction bottle. Remove the ice bath and react at room temperature for about 6 hours. Dichloromethane was distilled off, the reaction liquid was transferred to a separatory funnel, a water-methanol mixed solution (400 mL, water: methanol volume ratio of 1:3) was added, n-heptane extraction (150 mL×3) was added, and shaken vigorously until The whole system is colorless and transparent, and the organic layer is combined. The organic layer was dried over anhydrous sodium sulfate, and the organic solvent was distilled off to obtain a colorless solid, that is, compound 10. The product was stored in the dark and the yield was 93.2%.

According to the analysis of related databases, 4654-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Chen Si; Shi Zeyu; Xiao Qiong; Zhang Xiang; Tian Yulin; Yin Dali; (13 pag.)CN111087356; (2020); A;,
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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. 41175-50-2, name is 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol, molecular formula is C12H15NO, 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. Recommanded Product: 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol

General procedure: To a solution of aldehyde 4a (200 mg, 0.391 mmol) in propionic acid was added 8-hydroxyjulolidine (148 mg, 0.782 mmol, 2 equiv) and PTSA (7 mg, 0.039 mmol, 0.1 equiv). The solution was protected from light and stirred at room temperature overnight. To the brown mixture was added a solution of chloranil (95 mg, 0.391 mmol, 1 equiv) in DCM (10 mL), the reaction turned dark and was allowed to stir overnight at room temperature. The dark purple solution was evaporated to dryness, dissolved in DCM and washed with a saturated solution of NaHCO3. The organic phase was dried over MgSO4, filtrated, and evaporated. The crude was purified by column chromatography on silica gel (gradient of 100% DCM to 9/1 DCM/methanol) to obtain 222 mg of 5a (61%) as a purple solid after lyophilization (from dioxane/water: 1/1). 1H NMR (300 MHz, CDCl3): delta 8.85 (s, 1H, NH), 8.54-8.52 (m, 1H, HPy), 7.88 (s, 1H, CH triazole), 7.68 (t, J=7.3 Hz, 1H, HPy), 7.24 (t, J=6.2 Hz, 1H, HPy), 7.13 (d, J=7.8 Hz, 1H, HPy), 6.99 (d, J=8.0 Hz, 1H, Ha), 6.93 (s, 2H, H7), 6.85-6.82 (m, 2H, Hb, Hc), 5.59 (s, 2H, NCH2Py), 4.77 (s, 2H, OCH2CON), 4.60 (d, J=5.6 Hz, 2H, CH2NCO), 4.28 (s, 4H, CH2COOMe), 3.76 (s, 6H, OMe), 3.52 (dt, J=10.9, 5.5 Hz, 8H, H1, H4), 3.03 (t, J=6.3 Hz, 4H, H6), 2.84-2.67 (m, 4H, H3), 2.15-2.07 (m, 4H, H5), 2.00-1.97 (m, 4H, H2). 13C NMR (75 MHz, CDCl3): delta 172.20 (CO ester), 168.31 (CO amide), 154.89, 154.67, 152.48, 151.21, 149.82, 149.36 (CHPy), 145.90, 141.17, 138.00 (CHPy), 127.33 (C7), 126.22, 123.86, 123.77 (Cb or Cc), 123.61 (CH triazole), 123.56 (CHPy), 122.62 (CHPy), 119.42 (Ca), 115.83 (Cb or Cc), 113.05, 105.37, 68.55 (OCH2CON), 55.33 (NCH2Py), 53.91 (CH2COOMe), 52.34 (OMe), 51.20 (C1 or C4), 50.66 (C1 or C4), 35.28 (CH2NCO), 27.79 (C3), 20.93 (C2), 20.18 (C6), 20.04 (C5). MS (ES+), calcd for C48H51N8O7+ [M]+ 851.4, found 851.4. HRMS (ES+), calcd for C48H51N8O7+ [M]+ 851.3875, found 851.3901.

With the rapid development of chemical substances, we look forward to future research findings about 41175-50-2.

Reference:
Article; Collot, Mayeul; Lasoroski, Aurelie; Zamaleeva, Alsu I.; Feltz, Anne; Vuilleumier, Rodolphe; Mallet, Jean-Maurice; Tetrahedron; vol. 69; 48; (2013); p. 10482 – 10487;,
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Reference of 3068-00-6, 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.

General procedure: To a solution of CoCl2 (0.6 mmol) in anhyd MeCN (4 mL), the selecteddialkyl acetal (1 mmol), TMSCl (1.1 mmol), and butane-1,2,4-triol (3 mmol) were added, with stirring, at r.t. At the end ofthe reaction, the mixture was extracted with EtOAc and the combinedextracts were washed with 5% NaHCO3. The organic layerwas dried (anhyd Na2SO4) and filtered, and the solvent was evaporatedunder vacuum. The oils obtained were purified by flash chromatographyto give the desired compounds.

The chemical industry reduces the impact on the environment during synthesis 3068-00-6, I believe this compound will play a more active role in future production and life.

Reference:
Article; Battisti, Umberto Maria; Sorbi, Claudia; Franchini, Silvia; Tait, Annalisa; Brasili, Livio; Synthesis; vol. 46; 7; (2014); p. 943 – 946;,
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Adding a certain compound to certain chemical reactions, such as: 5456-63-3, trans-2-Aminocyclohexanol hydrochloride, 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, SDS of cas: 5456-63-3, blongs to alcohols-buliding-blocks compound. SDS of cas: 5456-63-3

To a solution of 1-(4-carbamoylbenzyl)-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (0.15 g) obtained in Reference Example 4 in DMF (10 mL) were added (1,2-trans)-2-hydroxycyclohexylamine hydrochloride (0.08 g), 0-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (0.26 g) and triethylamine (0.19 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the precipitate was collected by filtration and dried. The precipitate was washed with diisopropyl ether to give the title compound (0.13 g) as a colorless solid. MS (ESI+): [M+H]+ 421.2 1H NMR (300 MHz, DMSO-d6) delta 1.16-1.41 (4H, m), 1.55-1.71 (2H, m), 1.82-1.93 (1H, m), 1.98-2.09 (1H, m), 3.35-3.47 (1H, m), 3.63-3.76 (1H, m), 4.79 (1H, d, J = 5.3 Hz), 5.96 (2H, s), 7.35 (3H, d, J = 8.0 Hz), 7.57-7.64 (1H, m), 7.78-7.89 (4H, m), 7.93 (1H, brs), 8.29 (1H, d, J = 8.0 Hz), 9.74 (1H, d, J = 7.6 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5456-63-3, trans-2-Aminocyclohexanol hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SAKAMOTO, Hiroki; SUGIMOTO, Takahiro; EP2821401; (2015); A1;,
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Electric Literature of 10029-04-6, 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 10029-04-6 as follows.

Using compound (T-4) (50.0 g) as a starting material, imidazole (28.7 g) and methylene chloride (800 ml) were placed in a reactor and cooled to 0 C.A solution of t-butyldiphenylchlorosilane (116.1 g) in methylene chloride (110 ml) was slowly added dropwise thereto, returned to room temperature and stirred for 12 hours.The reaction mixture was poured into water and the aqueous layer was extracted with dichloromethane.The organic layer formed simultaneously with water washing was dried over anhydrous magnesium sulfate.The solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography (volume ratio, heptane: ethyl acetate = 10: 1) to obtain Compound (T-17) (127.4 g; 90%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10029-04-6, its application will become more common.

Reference:
Patent; Jieenzhi Co., Ltd.; Jieenzhi Petrochemical Co., Ltd.; Tian Zhongyuzhi; Shi Yekuangyi; Jin Tengshishang; Di Tianhekuan; (145 pag.)CN107108457; (2017); A;,
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Related Products of 140373-17-7, 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 140373-17-7 as follows.

To a solution of 6-(naphthalen-2-yl)-4-oxo-4,5-dihydropyrazolo[1,5-a]pyrazine-2-carboxylic acid (Intermediate 3A, 100 mg, 328 pmol) and N,N-diisopropylethylamine (170 pi, 980 pmol) in DMF (5.0 ml) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (69.1 mg, 360 pmol) and 1-hydroxy-7-azabenzotriazole (22.3 mg, 164 pmol). The mixture was stirred at RT for 1H. Then, 2-amino-2-(4-fluorophenyl)ethanol (50.8 mg, 328 pmol) was added, and stirring was continued overnight at RT, followed by heating to 50C for 5 h. After cooling to RT, the mixture was poured into water, and the precipitate was collected by filtration, washed with water and dried to afford the title compound. Yield: 66.1 mg (44% of theory). LC/MS [Method 7]: Rt = 0.90 min; MS (ESIpos): m/z = 443 [M+H]+. 1H-NMR (400 MHz, DMSO-d6): d [ppm] = 11.88 (br. s, 1H), 8.64 (d, 1H), 8.39 (s, 1H), 8.23 (s, 1H), 8.04 (d, 1H), 8.01-7.96 (m, 2H), 7.89 (dd, 1H), 7.64-7.57 (m, 2H), 7.48-7.39 (m, 3H), 7.20-7.12 (m, 2H), 5.11-5.01 (m, 2H), 3.79-3.67 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,140373-17-7, its application will become more common.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; MUeLLER, Steffen; SCHOHE-LOOP, Rudolf; ORTEGA, HERNANDEZ, Nuria; SUeSSMEIER, Frank; JIMENEZ NUNEZ, Eloisa; BRUMBY, Thomas; LINDNER, Niels; GERDES, Christoph; POOK, Elisabeth; BUCHMUeLLER, Anja; GAUGAZ, Fabienne, Zdenka; LANG, Dieter; ZIMMERMANN, Stefanie; EHRMANN, Alexander, Helmut, Michael; GERISCH, Michael; LEHMANN, Lutz; TIMMERMANN, Andreas; SCHAeFER, Martina; SCHMIDT, Georg; SCHLEMMER, Karl-Heinz; FOLLMANN, Markus; KERSTEN, Elisabeth; WANG, Vivian; GAO, Xiang; WANG, Yafeng; (801 pag.)WO2019/219517; (2019); A1;,
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Reference of 10535-17-8 , The common heterocyclic compound, 10535-17-8, name is 1-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol, molecular formula is C18H22O6, 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.

The reaction was carried out in a glove box, and lignin dimer 3 (0.1 mmol, 33.4 mg) and photocatalyst lanthanum triflate (5 mol%) were weighed.Auxiliary tetrabutylammonium chloride (5mol%),Nitrogen source di-tert-butyl azodicarboxylate (1 mmol) and 2.0 mL of pyridine were placed in a 10 ml pressure-resistant tube.The reaction pressure tube is sealed and placed under a purple lamp at 380 nm.After stirring for 24 hours, after the lignin dimer 3 is completely converted,After separation by silica gel column chromatography (ethyl acetate: petroleum ether = 1:5, volume ratio), product 3,4-dimethoxybenzaldehyde (13.4 mg, yield 81%)And 1-[1-(2-methoxy)phenoxyethanol]-1,2-dicarboxylic acid diisopropyl ester-oxime(3) (28.3 mg, yield 71%).

The synthetic route of 10535-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin University; Zhang Yuetao; He Jianghua; Wang Yinling; (11 pag.)CN110156581; (2019); A;,
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Synthetic Route of 756520-66-8 , The common heterocyclic compound, 756520-66-8, name is 1-(2,6-Dichloro-3-fluorophenyl)ethanol, molecular formula is C8H7Cl2FO, 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.

In a 100mL single-necked flask,1.2 g (0.005 mol) of 2-amino-4-hydroxy-6-bromo-quinazoline was added,(0.0065 mol, 1.3 equiv) of benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate (BOP)Acetonitrile 20 mL,Stirred at room temperature,A solution of 1.1 mL (0.0075 mol, 1.5 equiv) of 1,8-diazabicycloundecyl-7- (DBU) was added to clarify the solution,After 10min reaction with solid precipitation,Join again1.56 g of 1- (3-fluoro-2,6-dichloro-phenyl) ethanol (0.0075 mol,1.5 equiv),0.4 g of NaH (60%) and 10 mL of acetonitrile,After stirring at room temperature overnight,Add 200mL H2O,Extract three times with 90 mL of ethyl acetate,Combine ethyl acetate,Evaporation of ethyl acetate,Got a white solid.The residue was purified by silica gel column chromatography (petroleum ether: dichloromethane: ethyl acetate = 2: 1: 2)Yield 55%.

The synthetic route of 756520-66-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southern Medical University; Wan Shanhe; Wang Guangfa; Wu Xiaoyun; Tian Yuanxin; Ye Ling; Li Zhonghuang; Zhang Tingting; Zhu Zhengguang; Jin Hong; Zhang Jiajie; (27 pag.)CN106565684; (2017); A;,
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Application of 2919-23-5, 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 2919-23-5 as follows.

A mixture of 2-chloro-5-nitropyridine (7.12 g, 45.0 mmol) and cyclobutanol (3.40 g, 47.2 mmol) in THF (30 mL) was vigorously stirred at 0 C. while NaH (1.18 g, 46.7 mmol) was added in three portions over 10-20 s under air (Caution: Extensive gas evolution). Reaction residue was rinsed down with additional THF (5 mL), followed by stirring under positive argon pressure in the ice bath for 1-2 more minutes. The ice bath was then removed and the brown homogeneous solution was stirred for 1 h. The reaction mixture was concentrated under reduced pressure at 80 C., taken up in 0.75 M EDTA (tetrasodium salt) (150 mL), and extracted with CH2Cl2 (1*100 mL, 1*50 mL). The combined organic layers were dried (Na2SO4), concentrated, taken up in MeOH (2*100 mL) and concentrated under reduced pressure at 60 C. to provide the title compound as a thick dark amber oil that crystallized upon standing (7.01 g, 80%). 1H NMR (CDCl3) delta 9.04 (dd, J=2.84 and 0.40 Hz, 1H), 8.33 (dd, J=9.11 and 2.85 Hz, 1H), 6.77 (dd, J=9.11 and 0.50 Hz, 1H), 5.28 (m, 1H), 2.48 (m, 2H), 2.17 (m, 2H), 1.87 (m, 1H), 1.72 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2919-23-5, its application will become more common.

Reference:
Patent; Baumann, Christian Andrew; Gaul, Michael David; US2006/281755; (2006); A1;,
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