Category: alcohols-buliding-blocks

Electric Literature of 623-69-8 ,Some common heterocyclic compound, 623-69-8, molecular formula is C5H12O3, 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 NaH (0.366 g, 9.16 mmol) in THF (12 mL) at 0 °C was added 1 ,3- dimethoxy-2-propanol (1 g, 8.32 mmol) in THF (8 mL) solution. The mixture was warmed to room temperature and stirred for 0.5 hour. To this was added tosyl chloride (1.587 g, 8.32 mmol) in one portion. The white cloudy mixture was stirred at room temperature for 16 hours. LC/MS showed complete conversion. The reaction mixture was poured into water and extracted with EtOAc. The organic extracts were combined, washed with brine, dried with sodium sulfate and concentrated in vacuo to give 2 g of colorless oil. The crude mixture was purified by Analogix system (silica gel column 80 g, gradient: 0 min, 100percentn-heptane; 5-12 min, 20percent EtOAc in Heptane; 12-15 min. 30percent EtOAc in Heptane and hold until 30 min). The pure fractions were combined and concentrated in vacuo to give 1.25 g of product as colorless oil which solidified upon standing.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,623-69-8, its application will become more common.

Reference:
Patent; NOVARTIS AG; ANTONIOS-MCCREA, William, R.; BARSANTI, Paul, A.; HU, Cheng; JIN, Xianming; MARTIN, Eric, J.; PAN, Yue; PFISTER, Keith, B.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/66070; (2012); A1;,
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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. 671802-00-9, name is tert-Butyl 3-(2-hydroxyethoxy)propanoate. A new synthetic method of this compound is introduced below., name: tert-Butyl 3-(2-hydroxyethoxy)propanoate

Step 1: Synthesis of tert-butyl 3-{2-[(5-bromopyridin-2-yl)oxy]ethoxy}propanoate:[0692] To a stirred solution of 5-bromopyridin-2-ol (3.0 g, 17.24 mmol), tert-butyl 3-(2- hydroxyethoxy)propanoate (3.3 g, 17.19 mmol) and triphenylphosphine (6.8 g, 25.81 mmol) in tetrahydrofuran (120.0 mL) was added diethyl diazene-l,2-dicarboxylate (4.49 g, 25.78 mmol) dropwise at 0 C under an atmosphere of nitrogen. The resulting solution was stirred overnight at rt. The reaction mixture was concentrated under reduced pressure to give a crude residue, which was purified by silica gel flash chromatography (eluent: ethyl acetate/petroleum ether, v/v =1/3) to provide the titled product (yield: 50%) as colorless oil.

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, 671802-00-9, tert-Butyl 3-(2-hydroxyethoxy)propanoate.

Reference:
Patent; ARVINAS, INC.; JIN, Meizhong; CREW, Andrew, P.; DONG, Hanqing; WANG, Jing; SIU, Kam; FERRARO, Caterina; CHEN, Xin; QIAN, Yimin; (351 pag.)WO2016/118666; (2016); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 42514-50-1, name is 3-Amino-3-methylbutan-1-ol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H13NO

3-Amino-3-methyl-butan-1-ol (5.0 g, 0.04 mol) was dissolved in 150 mL CH2Cl2 and treated with di-tert-butyl dicarbonate (11.12 g, 0.05 mol). The resulting mixture was stirred for 18 h at 25 C. The mixture was concentrated to the desired material as an amber oil (9.8 g, 100%): 1H NMR (DMSO-d6) delta 3.55 (s, 1H), 4.43 (t, 1H, J = 5 Hz), 3.46 (m, 2H), 1.71 (t, 2H, J = 7 Hz), 1.37 (s, 9H), 1.12 (s, 6H).

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, 42514-50-1, 3-Amino-3-methylbutan-1-ol.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/99286; (2003); A1;,
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Application of 150192-39-5 ,Some common heterocyclic compound, 150192-39-5, 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.

(2-Bromo-5-methoxyphenyl)methanol (1 eq.) was dissolved in anhydrous DMF (1.1M solution) and imidazole (1.05 eq.) was added. To the stirred solution triisopropylsilyl chloride (1.1 eq.) was added and the resulting mixture was left stirring at RT for 8 h. All volatiles were evaporated in vacuo and the residual material was filtered with PE / EtOAc (9:1) over a pad of silica gel. After evaporation in vacuo the product was obtained as a colorless oil (94%), which was used without further characterization in the next reaction.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,150192-39-5, its application will become more common.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2007/129119; (2007); A1;,
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Electric Literature of 202865-66-5, 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. 202865-66-5, name is (2-Bromo-5-fluorophenyl)methanol, molecular formula is C7H6BrFO, 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.

Example 16 (1S,3’R,4’S,5’S,6’R)-6-[(4-ethylphenyl)methyl]-5-fluoro-3′,4′,5′,6′-tetrahydro-6′-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2′-[2H]pyran]-3′,4′,5′-triol [Show Image] [Show Image] 1) Synthesis of 5-bromo-2-fluoro-4-(hydroxymethyl)benzaldehyde; Tetramethylpiperidine (0.68 g, 4.87 mmol) was dissolved in tetrahydofuran (4.5 mL). To the resultant solution was added n-butyllithium (1.0 M n-hexane solution, 4.88 mL) at 0°C, and this solution was stirred for 15 minutes. The resultant mixture was cooled to -78°C and a solution of (2-promo-5-fluorophenyl)methanol (0.50 g, 2.43 mmol) in tetrahydrofuran (2.5 mL) was added dropwise thereto. The temperature of the solution was raised over 2 hours to -40°C. The solution was again cooled to -78°C, and then dimethylformamide (0.47 mL, 6.07 mmol) was added thereto. The temperature of the solution was raised to room temperature, and the solution was stirred for 30 minutes. Saturated aqueous ammonium chloride was then added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to thereby obtain the titled compound (604.3 mg, quantitative). 1H-NMR (CDCl3) delta: 4.78 (2H, s), 7.46 (1H, d, J=10.6 Hz), 8.01 (1H, d, J=6.2 Hz), 10.29 (1H, s).

According to the analysis of related databases, 202865-66-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP2048153; (2009); A1;,
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Related Products of 229027-89-8, 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. 229027-89-8, name is 2-Bromo-4-fluorobenzyl Alcohol, molecular formula is C7H6BrFO, 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 stirred solution of (2-bromo-4-fluorophenyl)methanol (10 g, 49 mmol, stepi) in tetrahydrofuran (50 mL) and toluene (50 mL) was added dropwise a 1.58 M solution of butyllithium in hexane (65 mL, 100 mmol) at -78 0C for 1 hour and the mixture was stirred for 2 hours at the same temperature. To the mixture was added dropwise a solution of ethyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate in tetrahydrofuran (10 mL) at -78 C for 10 minutes. This resulting mixture was slowly warmed up to room temperature and stirred for 19 hours at the same temperature. The reaction mixture was quenched by the addition of saturated ammonium chloride aqueous solution, and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1 ), to afford 7.1 g (45%) of the title compound as a white solid:1H-NMR (CDCI3) 57.19 (1 H, dd, J=8.4, 6.1 Hz), 6.98 (1 H, dd, J=11.2, 2.6 Hz), 6.90-6.80 (1 H, m), 4.79 (2H, s), 4.43-4.30 (2H, m), 4.25-4.06 (3H, m), 3.31 (1 H, s), 2.50-2.22 (4H, m), 2.05-1.85 (4H, m), 1.28 (3H, t, J=7.3 Hz); MS (ESI) 322 (M – H)-.

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 229027-89-8, 2-Bromo-4-fluorobenzyl Alcohol.

Reference:
Patent; PFIZER JAPAN INC.; PFIZER INC.; WO2006/134485; (2006); A1;,
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Application of 2215-78-3 ,Some common heterocyclic compound, 2215-78-3, molecular formula is C13H12O2, 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.

Manufacturing Example 34-1-1 1-Chloromethyl-4-phenoxy-benzene; To a solution of (4-phenoxy-phenyl)-methanol (408 mg, 2.04 mmol) in carbon tetrachloride (8.2 mL) was added triphenylphosphine (642 mg, 2.45 mmol) under nitrogen atmosphere at room temperature, and the reaction solution was stirred under reflux for 7 hours and 40 minutes. The reaction mixture was cooled to room temperature and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (409 mg, 92%).1H-NMR Spectrum (DMSO-d6) delta (ppm): 4.76 (2H, s), 6.98-7.05 (4H, m), 7.15-7.19 (1H, m), 7.39-7.46 (4H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2215-78-3, its application will become more common.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
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Related Products of 616-29-5, Adding some certain compound to certain chemical reactions, such as: 616-29-5, name is 1,3-Diaminopropan-2-ol,molecular formula is C3H10N2O, 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 616-29-5.

VII. 1 (3-tert-Butoxycarbonylamino-2-hydroxy-propyl)-carbamic acid tert-butyl esterDi-tert-butyl dicarbonate (41 .5g) was dissolved in dichloromethane (40.0 ml), a solution of 1 ,3- diamino-propan-2-ol (8.0g) and triethylamine (1 .5 ml) indichloromethane/methanol (1 :5; 100 ml) was added and the reaction mixture was stirred at room temperature overnight. The solution was concentrated in vacuo and the residue was dissolved in dichlormethane. The organic layer was washed with water, separated, dried and concentrated in vacuo. The residue was purfied by chromatography (silica / dichloromethane: methanol 25:1 ).Yield: 17 gESI mass spectrum: m/z = 291 (M+H)+

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. 616-29-5, 1,3-Diaminopropan-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HECKEL, Armin; HIMMELSBACH, Frank; KLEY, Joerg; LEHMANN-LINTZ, Thorsten; REDEMANN, Norbert; SAUER, Achim; THOMAS, Leo; WIEDENMAYER, Dieter; BLACK, Phillip; BLACKABY, Wesley; LINNEY, Ian; AUSTEN, Matthias; DANILEWICZ, John; SCHNEIDER, Martin; SCHREITER, Kay; WO2011/104340; (2011); A1;,
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Synthetic Route of 2516-33-8 ,Some common heterocyclic compound, 2516-33-8, molecular formula is C4H8O, 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 stirring solution/suspension comprised of N-hydroxyphthalimide (Aldrich, 57.15 g, 339.8 mmol), cyclopropanemethanol (Aldrich, 25.10 g, 341.1 mmol), and triphenylphosphine (“DEAD,” Aldrich, 91.0 g, 344 mmol) in 1.00 L of tetrahydrofuran under a nitrogen atmosphere and cooled to 6 C. (internal mixture temperature) with an ice-water bath was added diethyl azodicarboxylate (Aldrich, 56 ml, 356 mmol) dropwise over 20 minutes via addition funnel. The reaction mixture temperature was kept below 20 C. during the addition. Following addition of the DEAD, the cold bath was removed and the reaction mixture was stirred for 15 hours. The mixture was concentrated to a paste under reduced pressure. Chloroform (ca. 300 ml) was added and the mixture swirled to loosen all solids. Vacuum filtration removed the insolubles. The filtrate was likewise filtered to remove white precipitate that formed and to give a clear filtrate. Concentration under reduced pressure afforded a clear oil. Flash filtration through silica gel (100% chloroform) gave filtrates containing unseparated product. These filtrates were combined and concentrated under reduced pressure to afford 127.4 g of a clear oil. The oil was dissolved in absolute ethanol (400 ml) and the solution was refrigerated for two hours. A white crystalline solid had precipitated and was subsequently collected by vacuum filtration. The product was dried in the vacuum oven (60 C.) to afford 42.66 g (58%) of the desired material; m.p. 71-77 C.; 1H-NMR (400 MHz; CDCl3 signal offset to delta 6.96) delta 7.54-7.43 (m, 4H), 3.74 (d, 2H, J=7.6 Hz), 1.02-0.95 (m, 1H), 0.34-0.30 (m, 1H), 0.04-0.00 (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. 2516-33-8, Cyclopropylmethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Warner-Lambert Company; US7030119; (2006); B1;,
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Application of 4720-29-0 , The common heterocyclic compound, 4720-29-0, name is 3-(Benzylamino)-1-propanol, molecular formula is C10H15NO, 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.

1,1-bis(methylthio)-2-nitroethylene 9 (1.00 g, 6.06 mmol) was added to asolution of N-benzylamino-3-propan-1-ol 8a (1.00 g, 6.06 mmol) and DMAP (0.74 g, 6.06mmol) in t-butanol (20 mL). The resulting solution was heated to reflux for 24 h under nitrogenatmosphere. The reaction was monitored by TLC (CH2Cl2/MeOH, 97/3). After cooling to roomtemperature, the solvent was removed in vacuo to afford an oily residue which was purified byflash chromatography on silica gel (CH2Cl2/MeOH, 98/2) to give nitroacetamide 11a (oil, 0.42 g,28%), a mixture of (Z)- and (E)-isomers in a ratio close to 1/1.

The synthetic route of 4720-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fante, Bamba; Soro, Yaya; Siaka, Sorho; Marrot, Jerome; Coustard, Jean-Marie; Synlett; vol. 25; 7; (2014); p. 969 – 974;,
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