Category: alcohols-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 14002-80-3, Methyl 3-hydroxy-2,2-dimethylpropanoate, 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, Quality Control of Methyl 3-hydroxy-2,2-dimethylpropanoate, blongs to alcohols-buliding-blocks compound. Quality Control of Methyl 3-hydroxy-2,2-dimethylpropanoate

EXAMPLE 106a Preparation of intermediate 2,2-dimethyl-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester To a mixture of 3-hydroxy-2,2-dimethyl-propionic acid methyl ester (13.2 g, 0.1 mol), K2CO3 (20 g, 0.14 mol) and DMAP (6.2 g, 0.05 mol) in DCM (100 mL) was added p-toluenesulfonyl chloride (19 g, 0.1 mol). The mixture was stirred at room temperature overnight, then filtered. The filtrate was washed with HCl aq. (1 M) and water, dried over anhydrous Na2SO4 and concentrated to give the title compound (15 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14002-80-3, Methyl 3-hydroxy-2,2-dimethylpropanoate, and friends who are interested can also refer to it.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Yang, Song; Zhang, Jing; Zhang, Zhuming; US2009/156610; (2009); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 4139-61-1, 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.4139-61-1, name is 6-Bromo-4-hydroxycoumarin, molecular formula is C9H5BrO3, molecular weight is 241.04, as common compound, the synthetic route is as follows.

EXAMPLE 50 6-Bromo-4-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-1-benzopyran-2-one 6-Bromo-4-hydroxycoumarin (1.19 mmol, 0.287 g), K2CO3 (3.57 mmol, 0.493 g) and 2-3-(bromopropoxy)tetrahydro-2H-pyran (1.19 mmol, 0.264 g) is suspended in 10 mL of acetone, and is heated to 55 C. for 24 hrs at which time the reaction is not complete. Cs2CO3 (1.54 mmol, 0.5 g) and 5 mL of DMF are added and the reaction is heated for an additional 2 hrs. Twenty-five percent of the crude THP protected material is purified by HPLC to afford the title compound (70.8 mg, 62%); 1H NMR (CDCl3, 300 MHz) delta 7.91 (1H, d, J=2.25 Hz), 7.82 (1H, dd, J=2.5, 9 Hz), 7.39 (1H, d, J=9 Hz), 5.98 (1H, s), 4.59 (1H, m), 4.31 (2H, t, J=6 Hz), 3.83 (1H, m), 3.72 (1H, m), 3.55 (2H, m), 2.09 (2H, m), 1.65 (2H, m), 1.45 (4H, m); MS (ESI, Pos.) calcd for C17H19BrO5 m/z [M+H]=383.0, found 383.1.

The chemical industry reduces the impact on the environment during synthesis 4139-61-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/54681; (2005); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 2867-59-6, 3-Aminobutan-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, 2867-59-6, blongs to alcohols-buliding-blocks compound. name: 3-Aminobutan-1-ol

A mixture of 2,4-dichloro-6-nitro-quinazoline (80 mg, 0.33 mmol), THF (3.3 mL), 3- aminobutan-1-ol (35 mg, 0.39 mmol) and DIPEA (0.14 mL, 0.82 mmol) was stirred at RT for lh. LCMS (Method T2) Rt = 1.18 mins, mlz 297.08 [M+H]. Acetic acid (4 mL) was added directly to the mixture which was stirred at 70 00 for 16h. LCMS (Method T2) Rt = 0.85 mins, mlz 279.08 [M+H]. The solution was concentrated and the residue was taken up in methanol (5 mL). The solution was then purified using SCX-2 cartridge. The product was eluted with methanolic ammonia, affording 4-[(3-hydroxy-1-methyl-propyl)amino]-6-nitro-1 H-quinazolin-2- one (50 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2867-59-6, its application will become more common.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; LLOYD, Matthew Garth; (360 pag.)WO2018/215798; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 23147-58-2 , The common heterocyclic compound, 23147-58-2, name is Glycerol aldehyde dimer, molecular formula is C4H8O4, 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.

Step 1: 2-(2-hydroxyethyl)-5-methoxy-1-indanone A solution of 5-methoxy-1-indanone (500 mg, 3.08 mmol) in methanol (10 mL) was treated with 10% palladium on carbon (53 mg) followed by glycoaldehyde dimer (370 mg, 3.08 mmol) and 0.5M sodium methoxide in methanol (1.3 mL, 0.65 mmol). The mixture was placed under a hydrogen atmosphere (balloon) and stirred vigorously at room temperature for 65 hours. After purging with nitrogen, the mixture was filtered through a 0.45 mum Acrodisc and the disk was rinsed with methanol (2 mL). The filtrate was diluted with EtOAc (25 mL), washed with 0.1N HCl (15 mL) and brine (15 mL), dried over MgSO4, filtered, and evaporated under vacuum to a solid. LC-MS of this material showed a mixture of starting material (major) and product. The mixture was purified by chromatography on a Biotage Flash 12M KP-Sil column (12 mm*15 cm). The column was eluted with 3:2 EtOAc-hexanes, collecting 6 mL fractions every 30 sec. Fractions 20-36 were concentrated under vacuum and flashed with benzene to afford 2-(2-hydroxyethyl)-5-methoxy-1-indanone as an oil. 1H NMR (CDCl3, 500 MHz) delta 1.80 and 2.05 (two m, CH2CH2OH), 2.79 and 3.35 (two dd, 3-CH2), 2.83 (m, H-2), 3.77-3.90 (m, CH2CH2OH), 3.87 (s, OCH3), 6.86 (d, H-4), 6.89 (dd, H-6), and 7.67 (d, H-7).

The synthetic route of 23147-58-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wilkening, Robert R.; Fried, Amy; US2006/94779; (2006); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 3840-31-1, 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. 3840-31-1, name is (3,4,5-Trimethoxyphenyl)methanol. A new synthetic method of this compound is introduced below.

General procedure: The compound (3,4,5-trimethoxyphenyl)-methanol 15 (4.5 mmol) was dissolved in THF (15 mL) and added to a stirred suspension of NaH (60%, 5.4 mmol) in THF (5 mL) at 0 C. The reaction mixture was stirred for 30 min at the same temperature. Propargyl bromide (4.9 mmol) was added to the reaction mixture at the same temperature and stirring was continued for an additional 5 h at room temperature. After completion the reaction (TLC), the reaction mixture was quenched with ice water and extract with ethyl acetate (2 * 20 mL). The organic extract was washed with brine, dried over Na2SO4, and solvent removed under reduced pressure. The residue was subjected to silica gel column chromatography purification (ethyl acetate/hexane 1:10) to afford 1,2,3-trimethoxy-5-((prop-2-yn-1-yloxy)methyl)benzene 16.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3840-31-1, (3,4,5-Trimethoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Suman; Murthy, T. Ramalinga; Rajkumar; Srikanth; Dayakar; Kishor, Chandan; Addlagatta, Anthony; Kalivendi, Shasi V.; Raju, B. China; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 603 – 619;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 50595-15-8, 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 50595-15-8, name is tert-Butyl 2-hydroxyacetate. This compound has unique chemical properties. The synthetic route is as follows.

A stirred suspension of 88 mg (2.2 mmol) sodium hydride (60percent dispersion in mineral oil) in 5 ml of dry dimethylformamide at -5¡ã C. under nitrogen was treated with 264 mg (2 mmol) tert-butylglycolate. After 10 minutes 298 mg (2 mmol) of 3,6-dichloropyridazine (Aldrich D7, 320-0) was added and the solution was allowed to warm to room temperature and was stirred overnight. The volatiles were evaporated under reduced pressure and the residue was chromatographed on silica eluding with ethyl acetate/hexane (1:2) to give 210 mg of a gum that was dissolved in 20 ml of ethanol and treated with 10percent palladium on carbon (Fluka) and hydrogenated under a hydrogen atmosphere overnight. The catalyst was removed by filtration and the volatiles were evaporated under reduced pressure to give a gum that was chromatographed on silica eluding with ethyl acetate/hexane (1:2) followed by ethyl acetate to give 50 mg of a gum [M+H+MeCN]+252. The gum was dissolved in 2 ml of dichloromethane and treated with 1 ml of trifluoroacetic acid. After 10 minutes the volatiles were evaporated and the residue triturated with toluene and re-evaportated to give a gum that was further triturated with petroleum ether bp 40-60¡ã C. to give 2-(3-pyrazinyloxy)acetic acid trifluoroacetate.

According to the analysis of related databases, 50595-15-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US6472404; (2002); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 13807-89-1, name is 2-((4-Methoxybenzyl)oxy)ethanol. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-((4-Methoxybenzyl)oxy)ethanol

(1) Synthesis of ethylene glycol protected by azidochlorobenzyl group and methoxybenzyl group: synthesis of 1-azido-2-chloro-4-(4-methoxybenzyloxyethoxymethyl)benzene. 2-(4-Methoxybenzyloxy)ethanol (500 mg, 2.75 mmol) was dissolved in DMF (10 ml), and sodium hydride (60% in oil, 132 mg, 3.30 mmol) was added at 0 C., which was followed by stirring for 30 min. Then 4-azido-3-chlorobenzyl bromide (813 mg, 3.30 mmol) was added portionwise. The resulting mixture was stirred at 0 C. for 30 min and at room temperature for 2 hr. Ice-water was added and the mixture was extracted with ether. The ether layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to give the title compound as a yellow oil (805 mg, yield 84%). 1 H-NMR (270 MHz, CDCl3) delta: 7.39(d,1H), 7.30-7.24(m,3H), 7.13(d,1H), 6.90-6.85(m,2H), 4.51(s,4H), 3.80(s,3H), 3.64(s,4H)

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, 13807-89-1, 2-((4-Methoxybenzyl)oxy)ethanol.

Reference:
Patent; Wako Pure Chemical Industries, Ltd.; US5998595; (1999); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 945-24-4, name is (2,4-Diaminopteridin-6-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H8N6O

2,4-diamino-6-(hydroxymethyl)pteridine hydrochloride (4.40 g, 19.2 mmol) was dissolved in hot water (150 mL) and after cooling to 21 C the solution was neutralized with 1M NaOH aq. solution to pH 7 (ca. 20 mL) . The formed precipitates were collected by filtration, washed with water, and dried in vacuo over P205 to afford an orange-beige solid corresponding to 2,4-diamino-6- (hydroxymethyl)pteridine. The solid was suspended in dry DMAc (25 mL) and triphenylphosphine dibromide ( 18.1 g, 42.9 mmol) was added to the suspension. The turbid and dark mixture was stirred for 24 h at 20 C under a N2 atmosphere. Then 4-aminobenzoic acid (2.97 g, 19.6 mmol) was added to the reaction and stirred for 3 additional days. The reaction mixture was poured into 250 mL of 0.33M NaOH and the precipitate was filtered off. The filtrate was neutralized with 10% aq . acetic acid (ca. 20 mL and the precipitate form upon neutralization was filtered, washed with water, triturated with MeOH, filtered, and dried in vacuo to afford 7 as an orange-beige solid (5.70 g, 91%) . XH NMR (400 MHz, DMSO-d5) delta 12.15 (br s, 1H), 8.63 (s, 1H), 8.17 (br s, 1H), 7.94 (br s, 1H), 7.73 (d, J = 9.0 Hz, 2H), 7.04 (br s, 2H), 6.83 (d, J = 9.0 Hz, 2H), 4.81 (s, 2H), 3.23 (s, 3H); 13C NMR (101 MHz, DMSO-d5) delta 167.8, 163.2, 161.1, 152.3, 149.5, 147.8, 131.5, 122.2, 118.1, 111.7, 100.0, 55.2, 39.6.

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, 945-24-4, (2,4-Diaminopteridin-6-yl)methanol.

Reference:
Patent; DANMARKS TEKNISKE UNIVERSITET; PEIRO CADAHIA, Jorge; CLAUSEN, Mads, Hartvig; BONDEBJERG, Jon; HANSEN, Christian, Abildgaard; (101 pag.)WO2018/37120; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 110-73-6, 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. 110-73-6, name is 2-(Ethylamino)ethanol. A new synthetic method of this compound is introduced below.

To a vial containing 6-[4-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)piperidin-1-yl]nicotinic acid (63.07 mg, 0.15 mmol) was added 0.375 mL of DMA, EDC (31.6 mg, 0.16 mmol), HOBt (20.3 mg, 0.15 mmol), NMM (0.04 mL, 0.37 mmol) and 2-(ethylamino)ethanol (13.4 mg, 0.15 mmol). The reaction mixture was stirred at room temperature for 12 hours and then diluted with water and ethyl acetate. The layers were separated and the organic layer collected and concentrated to give an oil, which was purified by RP-HPLC to give N-ethyl-6-[4-({[6-(3-fluorophenyl)pyridin-3-yl]carbonyl}amino)piperidin-1-yl]-N-(2-hydroxyethyl)nicotinamide (32 mg, 43%). HRMS (TOF, ES+) calculated for C27H30FN50 +H: 492.2333; observed 492.2611.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,110-73-6, 2-(Ethylamino)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Blake, Tanisha D.; Hamper, Bruce C.; Huang, Wei; Kiefer, James R.; Moon, Joseph B.; Neal, Bradley E.; Olson, Kirk L.; Pelc, Matthew J.; Schweitzer, Barbara A.; Thorarensen, Atli; Trujillo, John I.; Turner, Steven R.; US2008/146569; (2008); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 722-92-9, 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.722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, molecular formula is C9H7F6NO, molecular weight is 259.15, as common compound, the synthetic route is as follows.

i) To a solution of 2-(5-bromopyridin-2-yl)acetic acid (500 mg) in DCM (4 mL) were added 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (625 mg), EDCl (476 mg) and DMAP (57 mg). The reaction mixture was stirredat RT for 1 hour, poured into water, filtered on a water repellent filter cartridge and concentrated under reducedpressure. The residue was purified by column chromatography on silica gel, using 10percent EtOAc in heptane as theeluent, followed by trituration with ether/pentane to obtain 820 mg of the expected compound. MS(ES+) m/z 456.9[M+H]+.

Statistics shows that 722-92-9 is playing an increasingly important role. we look forward to future research findings about 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol.

Reference:
Patent; Lead Pharma Cel Models IP B.V.; SANOFI; CALS, Joseph Maria Gerardus Barbara; NABUURS, Sander Bernardus; MACHNIK, David; SABUCO, Jean-Francois; SCHIO, Laurent; (49 pag.)EP3101005; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts