Category: alcohols-buliding-blocks

Synthetic Route of 2425-41-4, 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. 2425-41-4, name is (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol. A new synthetic method of this compound is introduced below.

under argon at 0 oC was added a solution of diol (S109, 4.92 g, 22.0 mmol) in THF (20 mL) dropwise; the resulting mixture was warmed to room temperature and stirred for 1h. The reaction mixture was cooled to 0 oC, a solution of propargyl bromide (18.6 g, 158.4 mmol) in THF (25 mL) was added slowly, and the resulting mixture was warmed to room temperature and stirred overnight at 40 oC. After the product was consumed, as observed by TLC, the reaction was quenched by dropwise addition of water at 0 oC, and the resulting mixture was extracted with dichloromethane (50 mL x 2). The combined organic layers were washed with brine and dried over anhydrous Na2SO4, filtered, and evaporated to give a residue, which was purified by flash silica gel column using ISCO companion (hexane/ethyl acetate, 0 – 30%) to give 5.92 g (89.5%) of compound S110 as an oil.1H NMR (500 MHz, CDCl3; ppm): d7.49-7.47 (dd, J 8.0, 1.5 Hz, 2H), 7.38-7.34 (m, 3H), 5.43 (s, 1H), 4.21 (d, J 2.5 Hz, 2H), 4.12 (t, J 2.5 Hz, 4H), 4.10 (s, 1H), 3.91 (s, 1H), 3.89 (s, 1H), 3.37 (s, 2H); ESI MS for C18H20O4 calculated 300.34, observed [M+H]+ 301.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2425-41-4, (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol, and friends who are interested can also refer to it.

Reference:
Patent; TOLLNINE, INC.; PONS, Jaume; WAN, Hong I.; BRADSHAW, Curt W.; SIM, Bang Janet; KUO, Tracy Chia-Chien; (239 pag.)WO2020/81744; (2020); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 2240-88-2, name is 3,3,3-Trifluoropropan-1-ol, molecular formula is C3H5F3O, 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. Safety of 3,3,3-Trifluoropropan-1-ol

A solution of DIAD (0.743 mL, 3.82 mmol) in THF (2.00 mL) was added slowly to a solution of 4-fluoro-3-nitrophenol (500 mg, 3.18 mmol), 3,3,3-trifluoropropan-l-ol (0.310 mL, 3.50 mmol) and PPli3 (1.00 g, 3.82 mmol) in THF (10.0 mL). The resulting reaction mixture was allowed to stir at RT overnight, after which TLC (20percent EtOAc in Hex) and LC-MS analysis showed product formation. Reaction mixture was concentrated under reduced pressure and residue purified by flash column chromatography: silica gel with a gradient of 5-20percent EtOAc in Hex to afford l-fluoro-2-nitro-4-(3,3,3-trifluoropropoxy)benzene (322 mg, 40.0 percent yield) as a clear golden oil. NMR (400 MHz, DMSO-ifc) d 7.68 (dd, J= 6.0, 3.2 Hz, 1H), 7.54 (dd, J= 10.9, 9.2 Hz, 1H), 7.42 (dt, J = 9.3, 3.5 Hz, 1H), 4.31 (t, .7= 5.9 Hz, 2H), 2.8l (qt, /= 11.4, 5.9 Hz, 2H). 19F NMR (376 MHz, DMSO-ifc) d -63.06 (t, J= 11.2 Hz, 3F), -129.28 (ddd, J= 10.3, 6.0, 3.6 Hz, IF). LCMS RT (Method 2) = 3.491 min.

With the rapid development of chemical substances, we look forward to future research findings about 2240-88-2.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; PONTIFICIA UNIVERSIDAD CATOLICA DE CHILE; SOUTHALL, Noel T.; VON BERNHARDI, Rommy M.; ALVAREZ, Alejandra; DEXTRAS, Christopher R.; DULCEY, Andres E.; MARUGAN, Juan J.; ZANLUNGO, Silvana; TALLEY, Daniel C.; FERRER, Marc; HU, Xin; (0 pag.)WO2019/173761; (2019); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 100-37-8 ,Some common heterocyclic compound, 100-37-8, molecular formula is C6H15NO, 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: An oven dried 10 mL round bottom flask equipped with a stir bar was brought into the glove box with a reflux condenser. The flask was charged with [RuHCl(CO)(HN(CH2CH2PPh2)2)] (4) (6.0 mg, 0.01 mmol, 1mol%), KOH (8.2 mg, 0.15 mmol, 15mol%), toluene (1.0mL), an amine (1 mmol, 1.0 equiv), and an alcohol (1mmol, 1.0equiv) in that order. After all reagents have been added to the flask, the reflux condenser was attached and secured with a Keck clamp. The top of the condenser was sealed with a septum and the whole apparatus was then removed from the glove box. Once outside the glove box, the apparatus was equipped to nitrogen flow by inserting an inlet needle supplying a positive pressure of nitrogen into the septum, and an outlet needle connected to an oil bubbler. The reaction mixture was heated at reflux in a silicone oil bath overnight (12h), then allowed to cool to rt, and the conversion determined by GC-MS (CI). The resulting residue was subjected to flash chromatography with the indicated solvent system to obtain the purified amide in the reported isolated yield.

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. 100-37-8, 2-(Diethylamino)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Oldenhuis, Nathan J.; Dong, Vy M.; Guan, Zhibin; Tetrahedron; vol. 70; 27-28; (2014); p. 4213 – 4218;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 2043-47-2, name is 1H,1H,2H,2H-Nonafluoro-1-hexanol. A new synthetic method of this compound is introduced below., Recommanded Product: 1H,1H,2H,2H-Nonafluoro-1-hexanol

First, 26.4 g of 2-(perfluorobutyl)ethanol and 75 ml of dehydrated methylene chloride were put in a 200 ml flask provided with a calcium chloride tube, and cooled to 5 C. Then, 35.27 g of trifluoromethanesulfonic anhydride was dropped to the mixture while being stirred. Subsequently, 12.65 g of triethylamine was dropped to the mixture while being stirred. After the dropping, the resultant mixture was stirred for 24 hours. The resultant reaction solution was washed with 30 ml of water, further washed with 30 ml of 3% sulfuric acid, again washed with 30 ml of water, and dried with sodium sulfate. The solvent was then distilled off. The residue was distilled (b.p. 88 C. to 90 C./28 mmHg), to obtain 35.26 g (Y: 91.8%) of 2-(perfluorobutyl)ethyl trifluoromethanesulfonate. The purity of the resultant compound was 94.2% as measured by GC.

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, 2043-47-2, 1H,1H,2H,2H-Nonafluoro-1-hexanol.

Reference:
Patent; Sharp Kabushiki Kaisha; Kanto Kagaku Kabushiki Kaisha; US6388146; (2002); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 2077-19-2, 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.2077-19-2, name is 2-(4-Bromophenyl)propan-2-ol, molecular formula is C9H11BrO, molecular weight is 215.09, as common compound, the synthetic route is as follows.

A flask was charged with 2-(4-bromophenyl)propan-2-ol (5.00 g, 23.3 mmol, Bioorg. Med. Chem. Lett. 2007, 17, 662), 4,4,4 45,5,55′-octamethyl-2,2′-bi(l,3,2- dioxaborolane) (6.49 g, 25.6 mmol), KOAc (6.84 g, 69.7 mmol), PdCl2(dppf) (0.949 g, 1.16 mmol) and DMSO (155 mL). The mixture was heated to about 80 C for about 4 h. After cooling to rt, the mixture was partitioned between brine (400 mL) and EtOAc (100 mL). The organic layer was isolated and the aqueous phase was extracted with two further portions of EtOAc (2 x 50 mL). The organic layers were combined, washed with brine (5 x 100 mL), dried over anhydrous MgS04 and concentrated in vacuo. The crude material was purified by silica gel flash chromatography with a gradient of 0 to 100% EtOAc/hexanes to give 2-(4-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)propan-2-ol (2.76 g, 45%): 1H NMR (d-DMSO) delta 7.80 (s, J = 8, 2H), 7.50 (s, J = 8, 2H), 1.58 (s, 6H), 1.34 (s, 12H).

Statistics shows that 2077-19-2 is playing an increasingly important role. we look forward to future research findings about 2-(4-Bromophenyl)propan-2-ol.

Reference:
Patent; ABBVIE INC.; LI, Bin; BREINLINGER, Eric; DAVIS, Heather; HOEMANN, Michael; LI, Biqin; SOMAL, Gagandeep; VAN EPPS, Stacy; WANG, Lu; WO2014/169473; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 25574-11-2, 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.25574-11-2, name is 3-(4-Bromophenyl)propan-1-ol, molecular formula is C9H11BrO, molecular weight is 215.087, as common compound, the synthetic route is as follows.

Under a nitrogen atmosphere, DPPA (diphenylphosphoryl azide) (2 eq) and l,8-Diazabicycloundec-7-ene (DBU) (2 eq) were subsequently added to a cooled (0 C) solution of the corresponding alcohol (4) (1 eq) in dry Nu,Nu’- dimethylformamide (0.4 M). After 0.5 h. NaN3 (2 eq) was added and the reaction mixture was heated for 3 h. at 100 C. After cooling to room temperature, the reaction was worked up by dilution with water and extraction with diethyl ether (x5). The combined organic layers were washed with water (x2), brine (xl), dried over sodium sulfate and concentrated in vacuo. Finally the crude material was purified by column chromatography to give the desired azide 3-(l-(8-azidooctyl)-lH-l,2,3-triazol-4-yl)pyridine ; The title compound was prepared from (54) according to the general procedure of example 5, but the reaction mixture was heated to 50 C for 24 h. The crude material was purified by column chromatography using PE/EtOAc 98:2 as eluant, to give a colorless oil; yield 79%; IR (KBr) 2941, 2097, 1488, 1254, 1072, 1011, 831, 795 cm”1; 1H- MR (300 MHz, CDC13) delta 7.41 (dd, J = 6.4/1.8 Hz, 2-H), 7.06 (dd, J = 6.4/1.8 Hz, 2-H), 3.28 (t, J= 6.7 Hz, 2-H), 2.66 (t, J = 7.3 Hz, 2-H), 1.88(quint, J = 6.7 Hz, 2-H) ppm; 1 C-NMR (75 MHz, CDC13) delta 139.9, 131.7, 130.3, 120.0, 50.6, 32.2, 30.4 ppm.

The chemical industry reduces the impact on the environment during synthesis 25574-11-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITA DEGLI STUDI DEL PIEMONTE ORIENTALE “AMEDEO AVOGADRO”; GENAZZANI, Armando A.; TRON, Gian Cesare; GALLI, Ubaldina; TRAVELLI, Cristina; CUZZOCREA, Salvatore; GROSA, Giorgio; SORBA, Giovanni; CANONICO, Pier Luigi; WO2014/178001; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 13826-35-2 ,Some common heterocyclic compound, 13826-35-2, 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.

a. 3-Phenoxybenzaldehyde Chromium trioxide (3.00 g.) was added to a stirred solution of pyridine (4.75 g.) in dry methalene chloride (75 ml.), and stirring was continued for a further 15 minutes. 3-Phenoxybenzyl alcohol (1 g.) in methylene chloride (5 ml.) was added, the mixture stirred for a further 15 minutes, decanted and the residue washed with diethyl ether (100 ml.). The filtrate was washed with 55 sodium hydroxide solution (3 * 50 ml), 2.5 NHCl (50 ml.) and 5% sodium carbonate solution (50 ml.) and dried over Na2 SO4 to give 3-phenoxy-benzaldehyde. Alternatively the alcohol can be oxidized using Jones’ reagent, a similar yield of aldehyde being obtained.

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. 13826-35-2, (3-Phenoxyphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; National Research Development Corporation; US4024163; (1977); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 3279-95-6, 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 3279-95-6 as follows.

Preparation of (4R)-4-((3R, 5S, 6R, 7R, 10S, 13R)-6-ethyl-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenant hrene-17-yl)-N-(2-hydroxyethoxy)pentanamide 6alpha-Ethyl-chenodeoxycholic acid (OCA, 30 mg, 0.07 mmol) and compound 8-ii (6.5 mg, 0.085 mmoL) were dissolved in dichloromethane, and added with TBTU (40 mg, 0.11 mmoL) and DIPEA (30 muL, 0.21 mmoL) successively. The reaction solution was stirred at room temperature overnight. After TLC showed the disappearance of starting material, water was added, and the reaction solution was extracted with ethyl acetate. The organic phase was concentrated under reduced pressure and the residures were purified by column chromatography to obtain compound 8(10 mg, 30%). 1H NMR (400 MHz, MeOD) delta 3.95 – 3.85 (m, 1H), 3.74 (dt, J= 16.4, 4.7 Hz, 2H), 3.67 (s, 1H), 3.35 – 3.32 (m, 1H), 1.00 (d, J= 6.5 Hz, 3H), 0.95 – 0.89 (m, 6H), 0.72 (s, 3H). 13C NMR (101 MHz, MeOD) delta 172.75, 77.45, 71.80, 69.78, 59.02, 55.86, 50.29, 48.46, 45.57, 42.37, 41.77, 40.17, 39.65, 35.40, 35.25, 33.15, 33.04, 31.49, 29.87, 29.32, 27.90, 23.17, 22.36, 22.10, 20.59, 17.47, 10.85, 10.64.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3279-95-6, its application will become more common.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Shanghai Hansoh Biomedical Co., Ltd.; LU, Aifeng; ZHONG, Huijuan; LI, Chenghai; BAO, Rudi; LV, Aifeng; (40 pag.)EP3290429; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 558-42-9, 1-Chloro-2-methyl-2-propanol, 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, Product Details of 558-42-9, blongs to alcohols-buliding-blocks compound. Product Details of 558-42-9

To a suspension of I-47 (336 mg, 0.93 mmol) and potassium carbonate (154 mg, 1.12 mmol) in DMF (6 mL) is added 1-chloro-2-methyl-propan-2-ol (100 muL, 0.98 mmol). The reaction mixture is stirred at 80¡ã C. for 16 h then concentrated in vacuo. The residue is extracted with CH2Cl2, washed with saturated aqueous NH4Cl, dried with Na2SO4, filtered and concentrated in vacuo to afford I-104 (365 mg); m/z 434 [M+H].

The synthetic route of 558-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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.

1)Synthesis of 5-bromo-2-fluoro-4-(hydroxymethyl)benzaldehydeTetramethylpiperidine (0.68 g, 4.87 mmol) was dissolved in tetrahydrofuran (4.5 mL).To the resultant solution was added n-butyllithium (1.0 M n-hexane solution, 4.88 mL) at 0¡ã C., and this solution was stirred for 15 minutes.The resultant mixture was cooled to -78¡ã C. and a solution of (2-bromo-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¡ã C.The solution was again cooled to -78¡ã 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; US2011/275703; (2011); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts