Tag: M.W=100-200

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.153599-45-2, name is Methyl 3-(2-hydroxyethyl)benzoate, molecular formula is C10H12O3, molecular weight is 180.2, as common compound, the synthetic route is as follows.Computed Properties of C10H12O3

To a stirred solution of methyl 3- (2-hydroxyethyl) benzoate (10 g) in anhydrous dichloromethane (90 mL) at 0 C was added methanesulfonyl chloride (34 g, 299 mmol) And triethylamine (12 g, 118 mmol).The reaction was stirred at 0 C for 1 hour, quenched with water (50 ml)And extracted with ethyl acetate (100 ml x 3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 10% ethyl acetate in petroleum ether)To give 2.7 g of methyl 3- (2 – ((methylsulfonyl) oxy) ethyl) benzoate as a colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153599-45-2, Methyl 3-(2-hydroxyethyl)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; CHIA TAI TIANQING PHARMACEUTICAL GROUP CO., LTD.; DING, ZHAO ZHONG; WU, HAO; SUN, FEI; WU, LI FANG; YANG, LING; (97 pag.)TWI558709; (2016); B;,
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Electric Literature of 702-82-9, Adding some certain compound to certain chemical reactions, such as: 702-82-9, name is 3-Aminoadamantan-1-ol,molecular formula is C10H17NO, 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 702-82-9.

1) A mixed solution of 3-amino-1-adamantanol and 1-chloroacetyl-2-cyanopyrrolidine in a solvent was mixed with a suspension of a base and a catalyst and then preheated by a preheater;2) The preheated mixture enters the tubular reactor, the residence time of the material in the tubular reactor is 60min, and then the reaction liquid withdrawn from the tubular reactor is collected and filtered, washed and purified to obtain the product.The process parameters are as follows:The preheater temperature is 70 C, the tube reactor temperature is 70 C, and the flow rate of the material in the line is 0.5 m / s.The molar ratio of 3-amino-1-adamantanol to 1-chloroacetyl-2-cyanopyrrolidine was 2: 1,3-amino-1-adamantanol was 0.13 g / ml, 1-chloro The concentration of acetyl-2-cyanopyrrolidine was 0.068 g / ml, the molar ratio of potassium carbonate to 1-chloroacetyl-2-cyanopyrrolidine was 1: 1, the amount of potassium iodide was the same as that of 1-chloroacetyl The molar ratio of 2-cyanopyrrolidine was 0.5: 1, and the reaction solvent was 2-butanone.Under this operating condition, the yield of the Viglitin reaction was 85% and the amount of the disubstituted compound was 4.5%.

According to the analysis of related databases, 702-82-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Pharmaceutical Group Tsingtao Guofeng Pharmaceutical Co., Ltd.; Liu Zhenyu; Lu Weishen; Zu Jinxiang; Lv Yiqiang; Zhou Zhenyu; (7 pag.)CN104311467; (2017); B;,
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Related Products of 402-63-1, 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 402-63-1 as follows.

Example 97 1-(3-Fluorophenyl)ethyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}carbamate 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (97 mg) was added to toluene/triethylamine = 10/1 (10 ml), and the mixture was heated under reflux to prepare asolution. 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 (111 mg, yield 68%). 1H-NMR (CDCl3, 400 MHz): 8.41 – 8.47 (1H, m), 8.12 (1H, s), 7.55 – 7.62 (3H, m), 6.86 – 7.38 (7H, m), 6.65 (1H, d, J = 6.6 Hz), 5.88 (1H, 1, J = 6.6 Hz), 4.14 (3H, s), 4.08 (3H, s), 1.60 (3H, d, J = 6.6 Hz) Mass spectrometry value (ESI-MS, m/z): 463 (M++1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,402-63-1, its application will become more common.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1243582; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 623-04-1, (4-Aminophenyl)methanol, 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, Computed Properties of C7H9NO, blongs to alcohols-buliding-blocks compound. Computed Properties of C7H9NO

To a solution of (4-aminophenyl)methanol (2.0 g, 16.2 mmol) from step A and DMAP (0.40 g, 3.2 mmol)in DCM (50 mL) was added dropwise acetic anhydride (7.6 mL, 81.0 mmol) at 0 0C over 30 min. After stirring under nitrogen for 30 min, the solution was concentrated and extracted with DCM twice. The combined extracts were washed with water and brine, dried over Na2SO4 and concentrated. Column chromatography on silica (20% EA in PE) afforded the title compound as white solid (3.35 g, 100%). 1H NMR (CDCl3, 300 MHz): delta 7.51 (d, J = 8.1 Hz, 2H), 7.31 (d, J = 8.1 Hz, 2H), 5.05 (s, 2H), 2.16 (s, 3H), 2.08 (s, 3H). MS (ESI, Pos. 1.5 kV) m/z 230.0 (M+Na)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,623-04-1, (4-Aminophenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; SHANGHAI TARGETDRUG CO., LTD.; AVEXA LIMITED; WO2009/92293; (2009); A1;,
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Synthetic Route of 62058-03-1, 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 62058-03-1 as follows.

General procedure: To a solution of ethyl 1-phenyl-5-(2-methyl-4-oxobutan-2-yl)-1H-pyrazole-4-carboxylate 14b (45 mg, 0.15 mmol) in CHCl3 (9 mL) was added trans-5-hydroxy-2-adamantylamine (25 mg, 0.15 mmol), acetic acid (0.025 mL, 0.45 mmol) and sodium triacetoxyborohydride (85 mg, 0.45 mmol) at room temperature. After stirring at ambient temperature for 16 hours, the reaction mixture was quenched with aq. NaHCO3, extracted with CHCl3, and washed with aq. NaCl. The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was dissolved in methanol (0.30 mL), and added 1.0 N NaOH (0.22 mL, 0.22 mmol) at room temperature. After stirring at ambient temperature for 16 hours, the solvent was removed under vacuum. The mixture of the residue in CHCl3 (1.5 mL) and DIPEA (0.078 mL, 0.45 mmol) and HBTU (35 mg, 0.15 mmol) was stirred at room temperature. After 16 hours, the reaction mixture was quenched with aq. NaHCO3, extracted with CHCl3, and washed with aq. NaCl., then purified with column chromatography (silica gel, eluting with CHCl3/methanol) to give the title compound as a white solid (0.025 g, 42 percent yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62058-03-1, its application will become more common.

Reference:
Article; Udagawa, Shuji; Sakami, Satoshi; Takemura, Takahiro; Sato, Mikiya; Arai, Takahiro; Nitta, Aiko; Aoki, Takumi; Kawai, Koji; Iwamura, Tomokatsu; Okazaki, Seiji; Takahashi, Takehiro; Kaino, Mie; Bioorganic and Medicinal Chemistry Letters; vol. 23; 6; (2013); p. 1617 – 1621;,
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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. 768-95-6, name is Adamantan-1-ol, the common compound, a new synthetic route is introduced below. category: alcohols-buliding-blocks

Adamantane acetic acid (1.6 g, 8.2 mmol) was dissolved in 20 mL dichloromethane and treated with dimethylformamide (2 drops) and oxalyl chloride (2.1 mL, 24.7 mmol) dropwise. The reaction was stirred at ambient temperature for 18 hours, concentrated in vacuo, and placed under hard vacuum overnight to yield the product as an oil (quant.).

The synthetic route of 768-95-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SPG THERAPEUTICS, INC.; SHAPOSHNIK, Zory; (120 pag.)WO2018/204422; (2018); A1;,
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Application of 50411-26-2 ,Some common heterocyclic compound, 50411-26-2, molecular formula is C9H13NO, 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 object product (160 mg, 73%) was obtained in the same manner as in Example 36(3) and using 6-(1’H-spiro[indene-1,4′-piperidin]-1′-yl)pyridazine-3-carboxylic acid (150 mg) obtained in Example 36(2), 1-amino-3-phenylpropan-2-ol (91 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (150 mg) and hydroxybenzotriazole hydrate (120 mg).1H NMR (300 MHz, DMSO-d6) delta ppm 1.33 (d, J=13.37 Hz, 2H) 2.01-2.20 (m, 2H) 2.59-2.81 (m, 2H) 3.17-3.29 (m, 1H) 3.37-3.54 (m, 3H) 3.79-3.96 (m, 1H) 4.60 (d, J=13.56 Hz, 2H) 5.05 (d, J=5.65 Hz, 1H) 6.87 (d, J=5.65 Hz, 1H) 7.11-7.48 (m, 11H) 7.87 (d, J=9.42 Hz, 1H) 8.67 (t, J=5.75 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,50411-26-2, its application will become more common.

Reference:
Patent; Taniguchi, Takahiko; Miyata, Kenichi; Kubo, Osamu; US2010/69351; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 111-90-0, Diethylene Glycol Monoethyl Ether, 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, HPLC of Formula: C6H14O3, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C6H14O3

[00150] Copper (I) iodide (FW 190.45, 0.90 grams, 4.72 mmol), 1,10-phenanthroline (FW 180.21, 0.83 grams, 4.62 mmol), cesium carbonate (FW 325.82, 19.00 grams, 58.30 mmol), 1 ,2-diiodobenzene (FW 329.90, 7.50 grams, 22.70 mol), di(ethylene glycol) ethyl ether (FW 134.17, 9.18 grams, 68.40 mol) and 100 milliliters of dry xylene were charged in a 350 milliliter three necked round bottom flask. The reaction mixture was heated with stirring at reflux temperature for 20 hours under nitrogen. The resulting suspension was cooled to room temperature by adding 50 milliliters of toluene. Then reaction mixture was filtered through celite and alumina. The low boiling (xylene and toluene) component was removed by a rotary evaporator and high boiling component di(ethylene glycol) ethyl ether by air bath oven at 200C under high vacuum for 2 hours. The residue was purified by flask chromatography on silica gel. The final dark yellow product yielded 7.00 grams (90%). The product I and C NMR analysis shows the formation of aryl ether product. IR: neat (cm” FontWeight=”Bold” FontSize=”10″ ): 745, 843, 931, 1052, 1 1 16, 1219, 1256, 1325, 1350, 1373, 1453, 1501, 1593, 2869, 2929, 2973. 1H NMR (CDC13): delta 6.76 (m, 4H, Ph), 4.02 (t, 4H, -OCH2-), 3.71 (m, 4H, -CH2O-) 3.57 (m, 4H, -OCH2), 3.45(m, 4H, -OCH2-), 3.37(t, 4H, -OCH2-), 1.06 (t, 6H, -CH3). 13C NMR (CDC13): 149.42, 121.61, 1 15.04, 70.89, 69.89, 69.76, 68.93, 66.59, 15.14.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,111-90-0, Diethylene Glycol Monoethyl Ether, and friends who are interested can also refer to it.

Reference:
Patent; EXXONMOBIL RESEARCH AND ENGINEERING COMPANY; PATIL, Abhimanyu, Onkar; BODIGE, Satish; WO2015/60985; (2015); A1;,
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Reference of 3360-41-6, 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. 3360-41-6, name is 4-Phenylbutan-1-ol. A new synthetic method of this compound is introduced below.

A CH2Cl2 solution (25 mL) of PPh3 (1.97 g,7.50 mmol) and I2 (1.90 g, 7.50 mmol) was stirred for 10 min at room temperature.Imidazole (851 mg, 12.5 mmol) was added to the resulting mixture. After a 10 min,4-phenylbutan-1-ol (751 mg, 5.00 mmol) was added to the mixture, and the resultingmixture was further stirred for 2 h. The mixture was quenched by the addition of satd.Na2S2O5 (25 mL). The aqueous and organic layers were separated, followed byextraction of the aqueous phase with CH2Cl2 (25 mL x 3). The combined organic phases were dried over anhydrous MgSO4, and the solvent was evaporated under reducedpressure. The crude product was purified by silica gel chromatography (eluent:hexane/AcOEt = 95/5) to give 4-iodobutylbenzene (1.14 g, 88%) as colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3360-41-6, 4-Phenylbutan-1-ol, and friends who are interested can also refer to it.

Reference:
Article; Sakai, Norio; Kobayashi, Taichi; Ogiwara, Yohei; Chemistry Letters; vol. 44; 11; (2015); p. 1503 – 1505;,
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Application of 7250-55-7, 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.7250-55-7, name is Dimethyl 3-hydroxypentanedioate, molecular formula is C7H12O5, molecular weight is 176.17, as common compound, the synthetic route is as follows.

Example 1 (Synthesis of dimethyl 3-benzyloxycarbonyloxyglutarate) In 10 ml of 1,2-dichloromethane was dissolved 1.01 g (5.78 mmol) of dimethyl 3-hydroxyglutarate, 847 mg (6.93 mmol) of 4,4-dimethylaminopyridine and 990 mul (6.93 mmol) of benzyloxycarbonyl chloride were added to the solution at room temperature, and the mixture was reacted at 0C for 30 minutes, and at room temperature for 1 hour under stirring. After completion of the reaction, the obtained reaction mixture was concentrated under reduced pressure, and the organic layer was extracted by adding 20 ml of ethyl acetate and 10 ml of water. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain an oily substance.

Statistics shows that 7250-55-7 is playing an increasingly important role. we look forward to future research findings about Dimethyl 3-hydroxypentanedioate.

Reference:
Patent; Ube Industries, Ltd.; EP1500642; (2005); A1;,
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