Category: alcohols-buliding-blocks

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.100-86-7, name is 2-Methyl-1-phenyl-2-propanol, molecular formula is C10H14O, molecular weight is 150.22, as common compound, the synthetic route is as follows.category: alcohols-buliding-blocks

100.6 ml of concentrated sulfuric acid (9.4 eq.) are placed in a 500 ml three-necked flask equipped with a condenser and a thermometer, followed by cooling to a temperature in the region of 5- 10C. A mixture containing 30 g of methyl- 1 -phenyl-2-propanol (1 eq.) and 9.83 g of acetonitrile (1 eq.) is added dropwise. The mixture is stirred for 5 minutes at a temperature in the region of 5-10C and then for 5 hours at room temperature (monitoring by TLC, 95/5 CH2Cl2/MeOH). (0210) The mixture is then poured into 1 litre of water and extracted with 100 ml of toluene. The aqueous phase is basified to pH 8.5 with ammonium carbonate and then extracted twice with 500 ml of MTBE (methyl tert-butyl ether). The organic phase is dried over Na2S04, filtered, evaporated to dryness and then dried under vacuum over P205. 27 g (78% yield) of compound (a) are obtained in the form of a yellow liquid. (0211) The NMR and mass analyses are in accordance with the expected structure.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-86-7, 2-Methyl-1-phenyl-2-propanol, and friends who are interested can also refer to it.

Reference:
Patent; L’OREAL; SABELLE, Stephane; FADLI, Aziz; CHARRIER, Alexandra; (47 pag.)WO2017/109185; (2017); A1;,
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Reference of 6240-11-5, 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. 6240-11-5, name is 1-Adamantaneethanol. A new synthetic method of this compound is introduced below.

In a 1 L round bottom flask equipped with a reflux condenser, 126.20 g (0.70 mol) of 2- (1-adamantyl) ethanol was added while 164 g of concentrated sulfuric acid and 200 g (48% aqueous solution) of hydrobromic acid were cooled in an ice bath, . The mixture was refluxed for 6 hours, cooled to room temperature and then added to 400 g of ice. The aqueous phase was extracted with 400 ml of pentane. The organic phase was washed with 2 M NaOH solution and water, dried over magnesium sulfate and the solvent was removed in vacuo. The product was distilled in vacuo to give 153.2 g (90%) of (1- (2-bromo-ethyl) -adamantane as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6240-11-5, its application will become more common.

Reference:
Patent; LUMMUS NOVOLEN TECHNOLOGY GMBH; (91 pag.)JP6196581; (2017); B2;,
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Synthetic Route of 6850-65-3, 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. 6850-65-3, name is 4-Aminocyclohexan-1-ol(isomers mixture), molecular formula is C6H13NO, 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 procedures for the preparation of l,l-difluoro-4-isocyanocyclohexane F. p HCOOEt F-?^| O PPh3 p ” tauAlpha ” ^^N^H ” v ,N. H NC Step A: Tert-but l 4-hydrox cyclohexylcarbamate. To a solution of 4-aminocyclohexanol (23 g, 0.2 mol) and Et3N (60 g, 0.6 mol) in THF (230 mL) was added (Boc)20 (87 g, 0.4 mol). The resulting solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with water (2 x 200 mL) and brine (200 mL), dried over anhydrous Na2S04 and concentrated. The residue was purified by column chromatography on silica gel using DCM/ MeOH (V:V, 20: 1) to afford the desired product as a white solid. MS: 216.2 (M+l)+.

According to the analysis of related databases, 6850-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2013/107291; (2013); A1;,
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Reference of 7397-62-8 ,Some common heterocyclic compound, 7397-62-8, molecular formula is C6H12O3, 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 3-neck, 50 mL flask (equipped with a thermocouple, magnetic stirrer, heating mantle, reflux condenser, and N2 purge) was added the intermediate (4) from Part B (1.0 g, 2.79 mmol), ethylene glycol (7.0 g), [1,] 8-diazabicyclo [5.4. 0] undec-7-ene (“DBU”, 42 mg, 0.28 mmol, 0.1 equivalents relative to the intermediate (4) ), and butyl glycolate (5) (1.1 g, 8. [38] mmol, 3.0 equivalents relative to the intermediate (4) ). The resulting white slurry was heated to [80C,] and then stirred at this temperature for 4.9 hr. Although the slurry initially formed a light yellow solution during this heating, it formed a clear solution after 40 min of heating. Following the 4.9 hr heating period, deionized water was added over a 15 min period in an amount such that the mixture became slightly turbid. During this water addition, the temperature was maintained at [80C.] The resulting mixture was stirred for another hour at this temperature, and then allowed to cool naturally to room temperature. The resulting precipitate was filtered, washed with water [(2X10] mL), and air-dried for 1.3 hr to afford 1.10 g of light yellow crystals. Liquid chromatography analysis comparing these crystals with a pre-formed standard indicated the formation of the desired product (6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7397-62-8, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2003/104223; (2003); 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.23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol, molecular formula is C9H20O5, molecular weight is 208.25, as common compound, the synthetic route is as follows.SDS of cas: 23783-42-8

A THF solution (200 mL) of H(OCH2CH2)4OMe (12 g, 60 mmol) and a stir bar was placed in a threenecked flask (500 mL). NaH (60%, dispersion in Paraffin Liquid, 2.9 g, 72 mmol) was added to the solution, and the mixture was stirred at room temperature for 30 min. Allyl bromide (6.2 mL, 72 mmol) was slowly added to the resulting mixture at the same temperature with vigorous stirring. The solution was stirred overnight, and the remaining NaH and NaBr were filtered off. The obtained filtrate was concentrated to dryness in vacuo. The residue was dissolved in water (500 mL) and extracted with hexane (200 mL3) and then dichloromethane (200 mL3). The resulting organic layer was dried with MgSO4 and then further dried under vacuum to afford the title compound 1d as a colorless oil (14 g, 55 mmol, 92%) 1d: 1H NMR (600 MHz, C6D6): delta 5.82 (m, CH2CHCH2O, 1H), 5.23 (m, CH2CHCH2O, 1H), 5.01 (m, CH2CHCH2O, 1H), 3.82 (m, CH2CHCH2O, 2H), 3.50-3.43 (m, CH2, 12H), 3.42-3.40 (m, CH2, 2H), 3.34 (m, CH2, 2H), 3.12 (s, OCH3, 3H). 13C{1H} NMR (150 MHz, C6D6): 135.7, 115.9, 72.4, 72.1, 71.07, 71.04 (3), 71.0, 70.9, 70.0, 58.6. HRMS (ESI): m/z calcd for [C12H24O5Na]+ (M+Na): 271.1516; found 271.1506.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol, and friends who are interested can also refer to it.

Reference:
Article; Inomata, Koya; Naganawa, Yuki; Guo, Haiqing; Sato, Kazuhiko; Nakajima, Yumiko; Tetrahedron Letters; vol. 60; 41; (2019);,
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Related Products of 67853-03-6, 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 67853-03-6 as follows.

To a solution of methyl 3-(hydroxymethyl)benzoate (3.0 g) obtained in the above-mentioned reaction and dihydropyran in acetonitrile was added p-toluenesulfonic acid monohydrate, and the mixture was stirred at room temperature for 1 day. Saturated aqueous sodium hydrogen carbonate solution was added, and acetonitrile was evaporated under reduced pressure. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column (5% ethyl acetate/hexane to 20% ethyl acetate/hexane) to give a brown oil (5.0 g). The object product was used for the next reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67853-03-6, its application will become more common.

Reference:
Patent; Taniguchi, Takahiko; Miyata, Kenichi; Kubo, Osamu; Matsui, Junji; US2009/325956; (2009); 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.27646-80-6, name is 2-Methyl-2-(methylamino)propan-1-ol, molecular formula is C5H13NO, molecular weight is 103.17, as common compound, the synthetic route is as follows.Recommanded Product: 2-Methyl-2-(methylamino)propan-1-ol

D16(a) 2-((2,6-dichloropyrimidin-4-yl)(methyl)amino)-2-methylpropan-l-ol 2-methyl-2-(methylamino)propan-l-ol (6.5 g, 63.0 mmol) in acetonitrile (50 mL) was added dropwise to solution of 2,4,6-trichloropyrimidine (11.56 g, 63.0 mmol) and triethylamine (8.78 mL, 63.0 mmol) in acetonitrile (100 mL) at 0 °C with stirring. The reaction mixture was stirred at 25 °C for 6 h, and then concentrated. EtOAc (20 mL) was then added. The organic phase was washed with water, brine, dried over sodium sulphate, and concentrated in vacuo. The residue was purified by silica gel column (PE/EA 5/1 to 3/1) to afford the title compound (2.5 g, 15.9percent) as a yellow solid. LC-MS (ESI): m/z 250 [M + H]+; 0.95 min (ret time).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,27646-80-6, 2-Methyl-2-(methylamino)propan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; SANG, Yingxia; WAN, Zehong; ZHANG, Qing; WO2014/114694; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3279-95-6, 2-(Aminooxy)ethanol, 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, Recommanded Product: 2-(Aminooxy)ethanol, blongs to alcohols-buliding-blocks compound. Recommanded Product: 2-(Aminooxy)ethanol

[0106] Step 3: To a solution of l-(4-(5-chloro-4-(5-methyl-lH-pyrazol-3- ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)ethanone (60 mg, 0.16 mmol) in MeOH (1 niL) was added AcOH (15 mg, 0.25 mmol), followed by the addition of 2- (aminooxy)ethanol (20 mg, 0.26 mmol). The mixture was heated to 60 0C for 14 h and cooled down to room temperature. The mixture was then purified directly by preparative RP-EtaPLC to provide l-(4-(5-chloro-4-(5-methyl-lH-pyrazol-3- ylamino)pyrimidin-2-ylamino)-2,5-dimethylphenyl)ethanone O-2-hydroxyethyl oxime; ESMS m/z 430.2 (M + H+).

The synthetic route of 3279-95-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2009/158431; (2009); A2;,
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Adding a certain compound to certain chemical reactions, such as: 764-48-7, Ethylene Glycol Vinyl 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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

10098] Compound 2, 1 -(6-(7-azabicyclo[2.2. 1]heptan-7- yl)naphthalen-2-yl)ethanone, was synthesized by the inventors.10099] Specifically, Compound 2c obtained in Example1-3 (184 mg, 0.61 mmol), palladium(II) acetate (Pd(OAc)2,6.8 mg, 0.03 mmol), diphenylphosphinopropane (DPPP,25.2 mg, 0.06 mmol), and ethyleneglycol (1.5 mE) were added to an oven-dried flask with two necks and charged with argon gas. Afier oxygen present in the mixture was removed by adding the argon gas to the mixture, ethyleneglycol vinyl ether (279 pL, 1.53 mmol) and Et3N (255 pL, 1.83 mmol) obtained by distillation were sequentially added thereto. The resulting mixture was stirred at 145 C. for 5 hours using a silicone oil container. The mixture was cooled to room temperature, and stirred with a 6N hydrochloric acid (HC1) aqueous solution (4 mE) at 60 C. for 4 hours. The mixture was cooled to room temperature, and diluted with ethyl acetate (100 mE). An organic layer was washed with water (50 mE), a 5% sodium bicarbonate aqueous solution (50 mE), and a saturated saline solution (50 mE) and dehydrated with anhydrous sodium sulfate (10 g). The solvent was removed under a reduced pressure condition of 40 mbar, and the resulting product was purified by colunm chromatography through a silica gel (Merck-silicagel 60, 230-400 mesh; using EtOAc/hexane as a developer), thereby obtaining a yellow solid, Compound 2 (100 mg, 62%). By further purification using recrystallization (using 3% CH2C12/hexane as a solvent), a yellow solid, Compound 2 (32 mg, 20%), was obtained.10100] ?H NMR (CDC13, 300 MHz, 298 K, oe): 8.32 (d, J=1.5 Hz, 1H), 7.93 (dd, J=8.7, 1.8 Hz, 1H), 7.78 (d, J=9.0 Hz, 1H), 7.64 (d, J=8.7 Hz, 1H), 7.24 (dd, J=8.7, 2.1 Hz, 1H), 7.11 (d, J=2.4 Hz, 1H), 4.37-4.34 (m, 2H), 2.67 (s, 3H),1.87-1.84 (m, 4H), 1.54-1.5 (m, 4H); ?3C NMR (CDC13, 75 MHz, 298 K, oe): 198.0, 148.6, 137.7, 131.9, 131.0, 130.4, 127.0, 126.7, 124.7, 119.8, 110.3, 58.3, 29.0, 26.7; IR (KBr, cm?): 1670; HRMS: mlz calcd for C,8H,9N0 [M] 265. 1467, C,8H2QNO [MH] 266.1545; found 265.1467 [M],266.1547 [MW]; mp: 118-120 C.

The synthetic route of 764-48-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; POSTECH ACADEMY-INDUSTRY FOUNDATION; AHN, Kyo Han; MOON, Hyunsoo; KIM, Dokyoung; SINGHA, Subhankar; ROY, Basab; SAMBASIVAN, Sunderraman; (45 pag.)US2017/327509; (2017); A1;,
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Synthetic Route of 629-30-1, 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 629-30-1, name is 1,7-Heptanediol. This compound has unique chemical properties. The synthetic route is as follows.

7- bromoheptane-l-ol1 (2): Heptane- 1,7-diol (36.0 g, 272 mmol; Alfa Aesar) and aq. 48percent HBr (38 mL, 0.9 equiv.) were heated under reflux in benzene (400 mL) with water removal using a Dean-Stark apparatus. After 16 h, all volatiles were removed in vacuo and the residue was purified by Si02 column chromatography using a gradient of 10-30percent EtOAc/hexanes as eluent to give 7-bromoheptan-l-ol (26.22 g, 62percent) as a colorless oil. TLC: 50percent EtOAc/hexanes, Rf ~ 0.40; NMR (400 MHz, CDC13) delta 3.61 (t, 2H, J = 7.1 Hz), 3.39 (t, 2H, J= 6.8 Hz), 1.80- 1.88 (m, 2H), 1.52-1.58 (m, 2H), 1.30-1.46 (m, 6H).

According to the analysis of related databases, 629-30-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MCW RESEARCH FOUNDATION, INC.; IMIG, John, David; CAMPBELL, William, B.; FALCK, John, Russell; WO2012/138706; (2012); A1;,
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