Category: alcohols-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 110-73-6, 2-(Ethylamino)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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

18a. Ethyl(2-(nitrooxy)ethyl)ammonium nitrate Ethyl(2-(hydroxy)ethyl)amine (5 g, 56 mmol) in EtOAc (60 mL) was added drop-wise to a mixture of fuming HNO3 (17.7 g, 11.8 mL, 280 mmol) and Ac2O (45.8 g, 42.3 mL, 448 mmol) at -10 C. The reaction mixture was stirred at -10 C. for 30 minutes and diluted with EtOAc and hexane. The oil layer was separated and dried in high vacuo to give the title compound (8.4 g, 76% yield) as a pale green oil. 1H NMR (300 MHz, d6-DMSO) delta 8.60-8.95 (bs, 2H), 4.84 (m, 2H), 3.37-3.49 (m, 2H), 3.02-3.16 (m, 2H), 1.24 (t, J=7.2 Hz, 3H). 13C NMR (75 MHz, d6-DMSO) delta 69.1, 43.6, 42.6, 11.0. Mass spectrum (API-TIS) m/z 135 (MH+).

The synthetic route of 110-73-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NitroMed, Inc.; US2004/24057; (2004); A1;,
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Adding a certain compound to certain chemical reactions, such as: 39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane, 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

Step 1: [1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanol 1,1-Bis(hydroxymethyl)cyclopropane (1.0 g, 0.0098 mol), triethylamine (TEA) (2.0 mL, 0.015 mol), and 1H-imidazole (0.13 g, 0.0020 mol) were dissolved in anhydrous DCM (15 mL) and the solution was cooled to 0 C. A solution of tert-butyldimethylsilyl chloride (1.55 g, 0.0103 mol) in DCM (5 mL) was added drop-wise and the resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 and extracted with DCM (3*). The organic extract was dried (magnesium sulfate), filtered, and concentrated in vacuo. The crude product was identified by 1H NMR and used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane, and friends who are interested can also refer to it.

Reference:
Patent; Yao, Wenqing; Burns, David M.; Chen, Lihua; Zhuo, Jincong; He, Chunhong; US2007/197506; (2007); A1;,
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Synthetic Route of 1805-32-9, 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. 1805-32-9, name is 3,4-Dichlorobenzyl alcohol. A new synthetic method of this compound is introduced below.

General procedure: Ionic liquid [Dsim]HSO4 (6.5 mg, ?0.02 mmol) was added to a stirred mixture of alcohol, phenol or naphthol (1.0 mmol) and HMDS (80 mg, 0.5 mmol) at room temperature under solvent free conditions. After completion of the reaction (monitored by TLC, It should be noted that when addition of HMDS is finished stirring of the mixture is stopped after 1 min. TLC showed that in most of the cases the reaction is completed immediately after the addition of HMDS), the product was extracted with Et2O and the ionic liquid was recovered and was dried at 65 ?C under vacuum to remove moisture, and then reused. Evaporation of the solvent under reduced pressure gave the highly pure product without further purification. The desired pure products were characterized by comparison of their IR, NMR and MS data as well as boiling poin twith those of known compounds

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1805-32-9, 3,4-Dichlorobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Article; Shirini, Farhad; Khaligh, Nader Ghaffari; Akbari-Dadamahaleh, Somayeh; Journal of Molecular Catalysis A: Chemical; vol. 365; (2012); p. 15 – 23;,
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Application of 149965-40-2, Adding some certain compound to certain chemical reactions, such as: 149965-40-2, name is (5-Bromo-2-chlorophenyl)methanol,molecular formula is C7H6BrClO, 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 149965-40-2.

5-Bromo-2-chlorophenyl)methanol (15.0 g, 67.7 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (27.5 g, 108 mmol), KOAc (19.9 g, 203 mmol), and 1,4-dioxane (100 mL) were added to a 250 mL round-bottomed flask under N2. The mixture was sparged with N2 for 5 minutes and then treated with Pd(dppf)Cl2.CH2Cl2 (4.96 g, 6.07 mmol). The mixture was sparged with N2 for another 5 minutes and then stirred at 100 C. for 16 hours before cooling to room-temperature. The resultant mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure to afford the product, which was purified by preparative HPLC (eluent: CH3CN/H2O and H2O with 0.04% NH3, 1:5 to 1:1, gradient elution) to afford pure product. The product was suspended in water (10 mL), the mixture frozen using dry ice/acetone, and then lyophilized to dryness to afford the title product (6.8 g) as a white solid. The white solid (6.8 g) was further purified by FCC (eluent:petroleum ether/ethyl acetate, 20:1 to 0:1) to afford the title compound (4.0 g, 22%). MS (ESI): mass calcd. for C13H18BClO3 268.1 m/z, found 251.0 [M-H2O+H]+. 1H NMR (400 MHz, CDCl3) delta 7.88 (s, 1H), 7.68-7.63 (m, 1H), 7.35 (d, J=7.9 Hz, 1H), 4.77 (d, J=6.4 Hz, 2H), 1.90 (t, J=6.6 Hz, 1H), 1.33 (s, 12H).

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. 149965-40-2, (5-Bromo-2-chlorophenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Janssen Pharmaceutica NV; Barbay, J. Kent; Chai, Wenying; Hirst, Gavin C.; Kreutter, Kevin D.; Kummer, David A.; McClure, Kelly J.; Nishimura, Rachel T.; Shih, Amy Y.; Venable, Jennifer D.; Venkatesan, Hariharan; Wei, Jianmei; (501 pag.)US2020/55874; (2020); 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.6642-34-8, name is (6-Bromobenzo[d][1,3]dioxol-5-yl)methanol, molecular formula is C8H7BrO3, molecular weight is 231.04, as common compound, the synthetic route is as follows.Application In Synthesis of (6-Bromobenzo[d][1,3]dioxol-5-yl)methanol

General procedure: To the solution of alcohol 4b (0.50 g, 2.67 mmol) and DMSO (0.41 g, 5.34 mmol) in ethyl acetate (5 ml) was added T3P (1.84 g, 6.68 mmol, 2.5 equiv, 50% solution in ethyl acetate) at 0 C. The resulting mixture was allowed to warm to RT and stirred for 1 h. Pyrazine-2-amine 3a (0.254 g, 2.67 mmol) was added to the above mixture and stirred for 15 min, which was followed by the addition of isocyanide 1c (0.33 g, 4.01 mmol) at room temperature and stirring for 4 h. Progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was diluted with ethyl acetate and neutralized with aqueous sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (25 mL ¡Á 2), the combined organic phases were washed with water, brine solution, dried over anhydrous sodium sulfate, and concentrated under vacuum to afford a crude product, which was purified on silica gel using ethyl acetate and petroleum ether.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6642-34-8, (6-Bromobenzo[d][1,3]dioxol-5-yl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Ramesha, Ajjahalli B.; Raghavendra, Goravanahalli M.; Nandeesh, Kebbahalli N.; Rangappa, Kanchugarakoppal S.; Mantelingu, Kempegowda; Tetrahedron Letters; vol. 54; 1; (2013); p. 95 – 100;,
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Application of 702-23-8, 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.702-23-8, name is 2-(4-Methoxyphenyl)ethanol, molecular formula is C9H12O2, molecular weight is 152.19, as common compound, the synthetic route is as follows.

To a solution of 4-methoxyphenethyl alcohol (1.03 g, 6.77 mmol) in dichloromethane (20 mL) were added N,N-diisopropylethylamine (2.3 mL, 14 mmol) and chloromethyl methyl ether (0.82 mL, 11 mmol) at 0 C. The reaction mixture was stirred for 27 h at ambient temperature. The reaction mixture was then concentrated under reduced pressure. Column chromatography (silica gel, 34 g; n-hexane/ethyl acetate, 8:1) gave the title compound (1.19 g, 6.07 mmol, 89.6%) as a pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ): delta 2.85 (t, J = 7.0 Hz, 2H), 3.30 (s, 3H), 3.72 (t, J = 7.0 Hz, 2H), 3.78 (s, 3H), 4.61 (s, 2H), 6.80-6.87 (m, 2H), 7.12-7.19 (m, 2H). 13 C NMR (100 MHz, CDCl 3 ): delta 35.5, 55.3, 55.4, 68.8, 96.5, 113.9, 129.9, 131.1, 158.2. HR-MS (EI): Calcd for C 11 H 16 O 3 [M] + : 196.1099. Found: 196.1093. IR (neat, cm -1 ): 2936, 2836, 1613, 1514, 1247.

Statistics shows that 702-23-8 is playing an increasingly important role. we look forward to future research findings about 2-(4-Methoxyphenyl)ethanol.

Reference:
Article; Karaki, Fumika; Kuwada, Miki; Tajiri, Saki; Kanda, Misaki; Yanai, Mari; Kamimura, Mitsuhiro; Itoh, Kennosuke; Fujii, Hideaki; Synthetic Communications; vol. 49; 2; (2019); p. 212 – 220;,
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Related Products of 61439-59-6, 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 61439-59-6, name is 2-(4-(Benzyloxy)phenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

B) To a solution of 2- (4-BENZYLOXY-PHENYL)-ETHANOL (78.72g, 0. 34MOL) in methylene chloride (400MUT) is added triethylamine (67. 3MOI, 0. 44MOL, 1.4eq), then at 0¡ãC is added mesylchloride (34. 8MOI, 0. 44MOL, 1.3eq). The reaction mixture is stirred at 0¡ãC for 30 minutes and allowed to rise to RT. The reaction mixture is extracted with methylene chloride (2 x 300MIS, the combined organic layers are then washed with brine (2 x 300MI) and concentrated under vacuum; To a solution of 2- (4-BENZYLOXY-PHENYL)-ETHANOL (78.72g, 0. 34MOL) in methylene chloride (400MI) is added triethylamine (67. 3ml, 0. 44MOL, 1.4eq), then at 0¡ãC is added mesylchloride (34. 8RNL, 0. 44MOL, 1.3eq). The reaction mixture is stirred at 0¡ãC for 30 minutes and allowed to rise to room temperature. The reaction mixture is extracted with methylene chloride (2 x 300ml), the combined organic layers are then washed with brine (2 x 300ml) and concentrated under vacuum. To the crude product in solution in ethyl acetate 600ml) is added sodium iodide (67.2g, 0. 44MOL, 1.3eq) and the reaction mixture is stirred under reflux for 6 hours. After filtration, the organic layer is washed with brine (3 x 00ml), dried with NA2SO4, filtered and concentrated under vacuum. 1-Benzyloxy-4-(2-iodo-ethyl)-benzene is isolated after crystallization with diethyl ether (116. 5g, 86percent).

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 61439-59-6, 2-(4-(Benzyloxy)phenyl)ethanol.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/21503; (2005); A1;,
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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 927-74-2, name is 3-Butyn-1-ol. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-Butyn-1-ol

To a stirred solution of the product of Preparation 17 (4.5 g, 16.3 mmol) in diethylamine (100 mL) was added but-3-yn-l-ol (1.9 mL, 32.6 mmol), Pd(PPh3)2Cl2 (500 mg, 1.63 mmol) and Cul (154 mg, 0.815 mmol) and resulting mixture was stirred for 17 h at room temperature. The solvent was then removed under reduced pressure and the residue was dissolved in diethyl ether (200 mL) and this solution was filtered to remove salts. The solvent was then removed under reduced pressure and the crude product was purified by silica gel chromatography (60 % EtOAc/Hexane) to afford the title intermediate (3.03 g, 91% yield).

With the rapid development of chemical substances, we look forward to future research findings about 927-74-2.

Reference:
Patent; THERAVANCE, INC.; WO2006/23457; (2006); A1;,
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Application of 534-03-2, 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 534-03-2, name is 2-Aminopropane-1,3-diol. This compound has unique chemical properties. The synthetic route is as follows.

Part I – Synthesis of 2-dibenzylamino-propane-1,3-diol [0316] Serinol (2.0 g, 22 mmol) and potassium carbonate (9.1 g, 66 mmol) were combined inethanol (50 mL). Benzyl bromide (5.2 mL, 44 mmol) was added and the reaction was stirred144wo 2013/169704 PCT/US2013/039839at reflux for 12 hours. The reaction mixture was concentrated, re-suspended in ethyl acetate,and washed with water and brine, dried (N a2S04), concentrated, and precipitated from etherto give 2-dibenzylamino-propane-1,3-diol. LCMS (ESI): calc. C17H21N02 = 271; obs. M+H= 272.

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 534-03-2, 2-Aminopropane-1,3-diol.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LYCERA CORPORATION; AICHER, Thomas; BARR, Kenneth; LAPOINTE, Blair; SIMOV, Vladimir; STEIN, Karin; THOMAS, William; TOOGOOD, Peter; VAN HUIS, Chad; WHITE, Catherine; WO2013/169704; (2013); A2;,
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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. 637031-88-0, name is 3,3-Difluorocyclobutanol. A new synthetic method of this compound is introduced below., COA of Formula: C4H6F2O

: A solution of 4′-bromo-6′- fluoro-r-(trifluoromethyl)spiro[l,3-dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine] (0809) (96.2mg, 0.2800mmol) and 2-(di-t-butylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-i-propyl-l,r- biphenyl (3.4 mg, 0.007 mmol) in l,4-dioxane (5.0 mL) was sparged with nitrogen for 3 mins. The reaction mixture was then treated sequentially with potassium hydroxide (47.3 mg, 0.84 mmol), water (101 pL, 5.62 mmol) and [2-(2-aminophenyl)phenyl]-methylsulfonyloxy- palladium; di-t-butyl-[3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (6.0 mg, 0.007 mmol) under continuous nitrogen stream. The vessel was sealed and heated to 80 C for 1 h and 30 min. The reaction mixture was quenched by the addition of acetic acid (64.3 pL, 1.13 mmol). The reaction mixture was poured into 75 mL of water and extracted with 4 x 20 mL EtOAc. The combined organics were dried with MgS04, filtered, and concentrated to dryness. The product was used without further purification (87 mg). During the reaction, some of the hydrodefluorinated product formed as an impurity. Data for 6-fluoro-l- (trifluoromethyl)-5,6-dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolan]-4-ol: LCMS ESI (+) (M+H) m/z 280. Data for l-(trifluoromethyl)-5,6- dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolan]-4-ol: LCMS ESI (+) (M+H) m/z 262.A solution of impure 6′-fluoro-r-(trifluoromethyl)spiro[l,3-dioxolane-2,7′- 5,6-dihydrocyclopenta[c]pyridine]-4′-ol (44.0 mg, 0.16 mmol), polymer supported (0812) triphenylphosphine (-2.06 mmol/g, 306.2 mg, 0.63 mmol), and 3,3-difluoro-cyclobutanol (68.1 mg, 0.63 mmol) in tetrahydrofuran (3.2 mL) was treated with diisopropyl (0813) azodicarboxylate (120 pL, 0.61 mmol) and stirred at 60 C for 2 h. The reaction mixture was filtered and the filter cake rinsed with 20 mL EtOAc. The filtrate was concentrated and purified by chromatography on silica using 10-30% EtO Ac/hexane to afford a clear solid (39.0 mg, 67%) that was a 2: 1 mixture of the fluorinated and hydrodefluorinated products. LCMS ESI (+) (M+H) m/z 370. Data for 4-(3,3-difluorocyclobutoxy)-6-fluoro-l- (trifluoromethyl)-5,6-dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolane]: LCMS ESI (+) (M+H) m/z 370. Data for 4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-5,6- dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolane]: LCMS ESI (+) (M+H) m/z 352.A solution of impure 4′-(3,3-difluorocyclobutoxy)-6′-fluoro-r-(trifluoromethyl)spiro[l,3- dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine] (39.0 mg, 0.106 mmol) in dichloromethane (2.0 mL) at 0 C was treated with perchloric acid (70% in water, 200 pL) and stirred at 0 C for 3 h. The reaction mixture was quenched by the addition of 5 mL of saturated aqueous (0817) NaHC03. The resulting mixture was extracted with 3 x 15 mL CH2Cl2. The combined organics were rinsed with 10 mL of brine, dried with MgS04, filtered, and concentrated to dryness. The product was used without further purification as a 2: 1 mixture of fluorinated and hydrodefluorinated ketones. LCMS ESI (+) (M+H) m/z 326. Data for 4-(3,3- difluorocyclobutoxy)-6-fluoro-l-(trifluoromethyl)-5,6-dihydro-7iT-cyclopenta[c]pyridin-7- one: LCMS ESI (+) (M+H) m/z 326. Data for 4-(3,3-difluorocyclobutoxy)-l- (trifluoromethyl)-5,6-dihydro-7i7-cyclopenta[c]pyridin-7-one: LCMS ESI (+) (M+H) m/z 308.A solution of impure 4-(3,3-difluorocyclobutoxy)-6-fluoro-l- (trifluoromethyl)-5,6-dihydrocyclopenta[c]pyridin-7-one (33.8 mg, 0.10 mmol) in dichloromethane (4.0 mL) was cooled to 0 C and sparged with nitrogen for 5 min. During this time formic acid (11.8 pL, 0.31 mmol) and triethylamine (28.8 pL, 0.21 mmol) were sequentially added. Once sparging was complete, RuCl(p-cymene)[(R,R)-Ts-DPEN] (1.3 mg, 0.002 mmol) was added under a continuous stream of nitrogen. The reaction vessel was sealed and placed into the refrigerator to react overnight. Volatiles were removed by concentration under reduced pressure. The residue was purified by chromatography on silica using 4-18% EtOAc/CH2Cl2 to afford ( 6R, 7L’)-4-(3 , 3 -difl uorocy d obutoxy )-6-fl uoro- 1 – (trifluoromethyl)-6,7-dihydro-5iT-cyclopenta[c]pyridin-7-ol (Compound 465) as a clear solid (5.4 mg, 16%) and (f?)-4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-6,7-dihydro-5i7- cyclopenta[c]pyridin-7-ol (Compound 466) as a clear solid (7.4 mg, 23%). Data for ( 6R,7S )- 4-(3, 3 -difl uorocycl obutoxy )-6-fluoro- l -(trifluoromethyl)-6,7-dihydro-5//- cyclopenta[c]pyridin-7-ol (Compound 465): Retention time HPLC (14 min) = 3.59 min; LCMS ESI (+) (M+H) m/z 328; 1H NMR (400 MHz, CDCl3): d 8.04 (s, 1H), 5.46-5.26 (m, 2H), 4.89-4.79 (m, 1H), 3.36-3.08 (m, 4H), 2.91-2.74 (m, 2H), 2.60 (dd, 1H). Data for (i?)-4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-6,7-dihydro-5iT-cyclopenta[c]pyridin-7- ol (Compound 466): Retention time HPLC (14 min) = 3.95 min; LCMS ESI (+) (M+H) m/z 310; 1H NMR (400 MHz, CDCI3): d 7.98 (s, 1H), 5.59-5.54 (m, 1H), 4.88-4.79 (m, 1H), 3.24- 3.07 (m, 3H), 2.89 (dd, 1H), 2.89-2.74 (m, 2H), 2.44-2.34 (m,…

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 637031-88-0, 3,3-Difluorocyclobutanol.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; JOSEY, John A.; SHRIMALI, Rajeev; WALLACE, Eli M.; WONG, Tai; (195 pag.)WO2019/191227; (2019); A1;,
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