Category: alcohols-buliding-blocks

Reference of 637031-88-0, 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. 637031-88-0, name is 3,3-Difluorocyclobutanol, molecular formula is C4H6F2O, 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 mixture of 3,3-difluorocyclobutanol (25.19 mg, 0.23 mmol) and A-107 (33 mg, 0.12 mmol) in 1,4-dioxane (4 mL) was added i-BuOK (26.15 mg, 0.23 mmol) at 20 C. The mixture was stirred at 20 C for 2 hours. The mixture was quenched with sat. NH4C1 (10 mL) and extracted with EtOAc (20 mL x 2). The combined organic phase was washed with brine (15 mL), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by prep-TLC (silica gel, PE:EtOAc = 1: 1) and prep-HPLC (Phenomenex Gemini (250 mm x 50 mm,10 _); A = H20 (0.05% NH4OH) and B = CH3CN; 55-65% B over 8 minutes) to afford Compound 86 (1.72 mg, 0.05 mmol) as a solid. 1H NMR (400MHz, CDCI3) _ = 9.59 (d, 1H), 8.75 (d, 1H), 8.36 (s, 1H), 8.20 (dd, 1H), 6.94 (d, 1H), 5.30-5.18 (m, 1H), 3.24-3.11 (m, 2H), 2.85-2.71 (m, 2H). LCMS R, = 1.14 min using Method A, MS ESI calcd. for [M+H]+ 372.1, found 372.0.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 637031-88-0, 3,3-Difluorocyclobutanol.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (364 pag.)WO2018/98499; (2018); A1;,
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Application of 19064-18-7, Adding some certain compound to certain chemical reactions, such as: 19064-18-7, name is (2,6-Difluorophenyl)methanol,molecular formula is C7H6F2O, 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 19064-18-7.

To a solution of 2.71 g of (2,6-difluorophenyl)methanol [CAS No.: 19064-18-7] (18.8 mmol, 1.3 eq.) in 120 ml of 1,2-dimethoxyethane were added 4.86 g of potassium tert-butoxide (43.3 mmol, 3.0 eq.) and the mixture was stirred at RT for 60 min. Subsequently, 2.60 g of 2-amino-3-chloro-5-methylpyrazine hydrochloride [CAS No.: 89182-14-9] (14.4 mmol, 1.0 eq.) were added and the mixture was stirred at 80 C. overnight. After cooling to room temperature, saturated aqueous sodium hydrogencarbonate solution was added and the aqueous phase was extracted three times with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried with magnesium sulphate, filtered and concentrated. The residue was purified by means of Biotage Isolera (340 g silica gel cartridge, cyclohexane/ethyl acetate gradient, 10%->72% ethyl acetate). 1.77 g of the title compound were obtained (39% of theory; 85% purity). (0942) LC-MS (Method 2): Rt=0.94 min (0943) MS (ESpos): m/z=252 (M+H)+ (0944) 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=2.20 (s, 3H), 5.35 (s, 2H), 5.88 (s, 2H), 7.09-7.23 (m, 2H), 7.37 (s, 1H), 7.46-7.57 (m, 1H).

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. 19064-18-7, (2,6-Difluorophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; FOLLMANN, Markus; HARTUNG, Ingo; BUCHGRABER, Philipp; JAUTELAT, Rolf; LINDNER, Niels; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; Dietz, Lisa; LI, Volkhart Min-Jian; (85 pag.)US2016/176880; (2016); A1;,
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Electric Literature of 1475-13-4 ,Some common heterocyclic compound, 1475-13-4, molecular formula is C8H8Cl2O, 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: A mixture of 4-chloro-2-trichloromethylquinazoline 1 (0.2 g, 0.71 mmol), DMAP (26 mg, 0.21 mmol, 0.3 equiv) and adequate alcohol derivative (0.85 mmol, 1.2 equiv) in toluene (3 mL) was introduced in miniaturized sealed reactor (5mL). The reaction mixture was irradiated in a monomode microwave oven, for 1 h at 130C. After removal of the toluene under reduced pressure, the residue was purified by silica gel column chromatography and recrystallized from appropriate solvent. 4.1.16 4-(1-(2,4-Dichlorophenyl)ethoxy)-2-(trichloromethyl)quinazoline (14) Yield 69%. Brown powder. Mp 123 C, (isopropanol). 1H NMR (200 MHz, CDCl3) delta = 8.31 (d, J = 8 Hz, 1H), 8.07 (d, J = 8 Hz, 1H), 7.96-7.87 (m, 1H), 7.69 (t, J = 7 Hz, 1H), 7.49-7.39 (m, 2H), 7.20 (dd, J = 2 Hz; 8 Hz, 1H), 6.78 (q, J = 7 Hz, 1H), 1.81 (d, J = 7 Hz, 3H) . 13C NMR (50 MHz, CDCl3) delta = 165.3, 159.2, 150.8, 135.3, 131.6, 130.8 129.4, 129.3, 129.0, 128.6, 123.4, 115.4, 96.9, 72.7, 21.0. LC-MS (ESI+) tR 6.02 min, m/z [M + H]+ 434.74/436.86/438.81. MW: 436.55 g/mol. Anal. Calcd for C17H11Cl5N2O: C, 46.77; H, 2.54; N, 6.42. Found: C, 46.41; H, 2.52; N, 6.51.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1475-13-4, its application will become more common.

Reference:
Article; Gellis, Armand; Primas, Nicolas; Hutter, Sebastien; Lanzada, Gilles; Remusat, Vincent; Verhaeghe, Pierre; Vanelle, Patrice; Azas, Nadine; European Journal of Medicinal Chemistry; vol. 119; (2016); p. 34 – 44;,
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Electric Literature of 558-42-9, 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 558-42-9, name is 1-Chloro-2-methyl-2-propanol. This compound has unique chemical properties. The synthetic route is as follows.

To the mixture of 6-(3-Bromo-5-chloro-4-hydroxyphenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one (Reference example 87, 300 mg) was dissolved in ethanol-water (4 : 1, 10 mL) were added 1-chloro-2-methyl-2-propanol (0.388 mL) and potassium carbonate (522 mg). The reaction mixture was refluxed for 8 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and filtrated, and the solvent was removed. The obtained crude product was purified by silica gel column chromatography (heptane : ethyl acetate = 67 : 33 to 33 : 67). The obtained solid was recrystallized from 2-propanol to afford the title compound as a white powder (107 mg).Melting point : 176.6-178.2°C

According to the analysis of related databases, 558-42-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KATOH, Takahiro; IIDA, Masatoshi; TERAUCHI, Yuki; YAMAGUCHI, Kazuya; HIROSE, Toshiyuki; YOKOYAMA, Fumiharu; NISHIMORI, Hikaru; OBUCHI, Yutaka; NABESHIMA, Hiroshi; TAKAKI, Emiri; (250 pag.)WO2017/150654; (2017); A1;,
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Reference of 17100-64-0 , The common heterocyclic compound, 17100-64-0, name is (4-Bromo-3-methoxyphenyl)methanol, molecular formula is C8H9BrO2, 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.

Intermediate Example Int 10.27.011 -bromo-4-(ch loromethy l)-2-methoxybenzeneTo a stirred solution (4-bromo-3-methoxyphenyl)methanol (660 mg) in DCM (20 mL) was added N,N-Diisopropylethylamin (1 .59 mL) and methanesulfonyl chloride (0.36 mL) and the mixture was stirred at r.t. for 16 h. A half-saturated solution of sodium bicarbonate was added and the mixture was extracted with DCM. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silicagel chromatography gave 700 mg of the title compound.

The synthetic route of 17100-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; SCHIROK, Hartmut; BRIEM, Hans; WO2012/143329; (2012); A1;,
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Reference of 764-48-7 ,Some common heterocyclic compound, 764-48-7, molecular formula is C4H8O2, 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 round bottom flask 1 L, 1,1′-thiocarbonyldiimidazole 3.6 g (20.2 mmol), 2-hydroxyethyl vinyl ether (95% purity) 1.9 mL (20.2 mmol) and toluene 60mL was added, 60 at was refluxed for 6 hours. Then allowed to cool to room temperature, potassium hydroxide 0.05g (0.89mmol) and benzyl mercaptan 2.4mL of (20.5 mmol) was added, and the mixture was refluxed for 6 hours again 60 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,764-48-7, its application will become more common.

Reference:
Patent; UNIVERSITYOF FUKUI; MARUZENPETROCHEMICAL COMPANY LIMITED; SUGIHARA, SHINJI; (22 pag.)JP5818142; (2015); B2;,
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Adding a certain compound to certain chemical reactions, such as: 24034-73-9, (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-ol, 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, name: (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-ol, blongs to alcohols-buliding-blocks compound. name: (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-ol

0441] 2E,6E,10E)-3)7,ll,15-tetramethylhexadeca-2,6,10i14-tetraen-l-yl 4- methylpiperazine-l-carboxylate (40a): To a solution of alcohol 1 (160 mg, 55 mmol) in DCM (3 mL) at 0 C was added carbonyldiimidazole (CDI) (107 mg, 0.66 mmol) and the reaction was stirred for 1 h. Then N-methylpiperazine (80 mg, 0.72 mmol) and DMAP (68 mg, 0.55 mmol) were added and stirred for 12 h. Solvent was removed and the residue was purified by column chromatography (DCM/ MeOH) to give the carbamate 40a as a viscous oil in 88 % yield (191 mg). TLC Rf: 0.54 (10% MeOH/DCM); JH NM R (300 MHz, CDCI3): delta 5.34 (t, 3H), 5.08 (m, 3H), 4.59 (d, 2H), 3.49 (m, 4H), 2.35 (m, 4H), 2.29 (s, 3H), 2.10-1.97 (m, 12H), 1.70 (s, 3H), 1.67 (s, 3H ), 1.59 (s, 9H); LCMS: MS (m/z): 417 (M+H ).

The synthetic route of 24034-73-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COYOTE PHARMACEUTICALS, INC.; SERIZAWA, Hiroaki; ARGADE, Ankush B.; DATWANI, Akash; SPENCER, Natalie; PAN, Yonghua; ERMINI, Florian; WO2013/130654; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 149104-89-2, (4-Bromo-3-methylphenyl)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, 149104-89-2, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C8H9BrO

3.7 g (43 mmol, 10 eq) of manganese dioxide are added to a solution of 900 mg (4.3 mmol, 1 eq) of (4-bromo-3-methylphenyl)methanol in 8 mL of dichloromethane. The reaction mixture is stirred for 12 hours at room temperature. The solid is filtered off and the solvent is evaporated off. 900 mg of 4-bromo-3-methylbenzaldehyde are obtained in oil form and used in the following 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,149104-89-2, its application will become more common.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2006/18326; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 372-30-5, Ethyl 4,4,4-trifluoro-3-hydroxybutyrate, 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, COA of Formula: C6H9F3O3, blongs to alcohols-buliding-blocks compound. COA of Formula: C6H9F3O3

(1) Protection of a hydroxyl group of ethyl 4,4,4-trifruolo-3-hydroxybutyrate with dihydropyran With stirring, 7 ml of conc. hydrochloric acid was added dropwise to a mixture of 33.4 g of R-(+)-ethyl 4,4,4-trifluoro-3-hydroxybutyrate and 22.6 g of dihydropyran under ice cooling. After the dropwise addition, stirring continued at room temperature for another 5 hours. The reaction mixture was poured into ice water, neutralized with sodium hydrogen carbonate, and then extracted with methylene chloride. After drying, the solvent was evaporated. The residue was distilled under reduced pressure of 6 mmHg to obtain 41.3 g of final ethyl 4,4,4-trifluoro-3-tetrahydropyranyloxybutyrate (1) (yield 85 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,372-30-5, Ethyl 4,4,4-trifluoro-3-hydroxybutyrate, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; US5264150; (1993); A;,
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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.647-42-7, name is 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol, molecular formula is C8H5F13O, molecular weight is 364.1, as common compound, the synthetic route is as follows.Computed Properties of C8H5F13O

The same fluoroalkyloxy alkanes as in Examples 1- 4 were prepared following an alternative procedure. A mixture comprising 0.1 moles of fluorinated alcohol, 60 ml of N-methyl-2-pyrrolidone, 0.2 moles of 1- bromoalkane, and 60 ml of a 45% aqueous solution of KOH was heated under stirring for 5 hours at 500C, then at 700C for 2 hours so as to complete the reac- tion. The raw reaction mixture was filtered so as to remove the formed KBr, and then diluted in 20 ml of water; the organic phase thus obtained comprised the desired fluoroalkyloxy alkane (yield: 80%) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,647-42-7, 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; ALChiMI.A. S.r.l.; WO2009/133575; (2009); A1;,
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