Category: alcohols-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 29683-23-6, Tetrahydro-2H-thiopyran-4-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, 29683-23-6, blongs to alcohols-buliding-blocks compound. Application In Synthesis of Tetrahydro-2H-thiopyran-4-ol

Step A. (l SJaS,6aR)-4-((2-fluoro-5-[2-methyl-6-(tetrahydro-2 H-thiopyran-4-yloxy)pyridin-3- yllbenzyl} oxy)- 1 , 1 a,6,6a-tetrahydrocvcloproparalindene- 1 -carboxylic acid To a solution of tetrahydro-2H-thiopyran-4-ol (56.6 mg, 0.48 mmol) in DMF (2 ml) at 0 C was added sodium hydride (60%, 19.2 mg, 0.48 mmol). The reaction mixture was stirred at 0 C for approximately 30 mins. (l S,laS,6aR)-4- {[2-fluoro-5-(6-fluoro-2-methylpyridin-3- yl)benzyl]oxy}- l, la,6,6a-tetrahydrocyclopropa[a]indene-l-carboxylic acid, ethyl ester from Example 1, Step B (100 mg, 0.24 mmol) was added to the reaction. The mixture was stirred at room temperature overnight. 1 ml of LiOH(lM) was added to the reaction and irradiated microwaves at 100 C for 1 hour. The pH of the mixture was adjusted to 7.0 with 1 N HCl. The residue was purified by preparative HPLC reverse phase (C-8), eluting with Acetonitrile/Water with 0.1 % of TFA to give the title compound. MS: m/e 488.1 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29683-23-6, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; LI, Bing; SZEWCZYK, Jason W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi P.; PIO, Barbara; DANG, Qun; LIN, Linus S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/89809; (2015); A1;; ; Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William, K.; LI, Bing; SZEWCZYK, Jason, W.; WANG, Bowei; PARKER, Dann; BLIZZARD, Timothy; JOSIEN, Hubert; BIJU, Purakkattle; CHOBANIAN, Harry; GUDE, Candido; NARGUND, Ravi, P.; PIO, Barbara; DANG, Qun; LIN, Linus, S.; HU, Bin; CUI, Mingxiang; CHEN, Zhengxia; DAI, Meibi; ZHANG, Zaihong; LV, Ying; TIAN, Lili; WO2015/95256; (2015); 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. 33420-52-9, name is 2,2-Difluoropropan-1-ol, molecular formula is C3H6F2O, 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. Product Details of 33420-52-9

To a solution of 2,2-difluoropropan-1-ol (1.30 g) in THF (25 mL) was added 60% sodium hydride (0.64 g) at0C, and the mixture was stirred at the same temperature for 20 min. To the reaction mixture was added methyl 4,6-dichloropyrimidine-5-carboxylate (2.55 g), and the mixture was stirred under an argon atmosphere at 0C for 1 hr. Thereaction mixture was diluted with ethyl acetate, and the organic layer was washed with saturated brine, and dried overanhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gelcolumn chromatography (ethyl acetate/hexane) to give the title compound (2.81 g).1H NMR (300 MHz, DMSO-d6) delta 1.70 (3H, t, J = 19.2 Hz), 3.92 (3H, s), 4.77 (2H, t, J = 12.8 Hz), 8.84 (1H, s).

With the rapid development of chemical substances, we look forward to future research findings about 33420-52-9.

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; SHIMOKAWA, Kenichiro; KOJIMA, Takuto; SAKAMOTO, Hiroki; FUJIMORI, Ikuo; NAKAMURA, Minoru; YAMADA, Masami; MURAKAMI, Masataka; KAMATA, Makoto; SUZUKI, Shinkichi; (78 pag.)EP3144308; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 722-92-9, 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. 722-92-9, name is 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol. A new synthetic method of this compound is introduced below.

To a suspension [OF 2- (4-AMINOPHENYL)-1,] 1,1, 3,3, 3-hexafluoropropan-2- ol (Oakwood, 8.4 g, 28.4 [MMOL)] in CH2CI2 (75 mL) was added trifluoroacetic anhydride (4.4 mL, 31.2 [MMOL)] via addition funnel over 30 min. After stirring at ambient temperature overnight, the reaction mixture was diluted with ethyl acetate and washed with water, saturated NaHCO3, and brine. The organics were dried [(MGS04),] filtered and concentrated to afford the intermediate amide as a white solid. The amide was dissolved in anhydrous THF (75 mL) and lithium aluminum hydride [(1 M SOLUTION] in THF, 75 mL) added over 30 min. After stirring at ambient temperature for 30 min, the solution was heated at reflux over 18 h. The reaction mixture was cooled to room temperature and quenched under argon with ethyl acetate. Water was carefully added and the resulting mixture stirred 30 min. The mixture was filtered through a pad of celite and the filtrate concentrated in vacuo. The resulting oil was dissolved in ethyl acetate and washed several times with brine. The organics were dried [(MGS04)] and concentrated to afford the title compound as a yellow oil (5.6 g, 58percent). MS (ES+) m/z 342 [(MH+).]

At the same time, in my other blogs, there are other synthetic methods of this type of compound,722-92-9, 2-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; PHARMACIA CORPORATION; WO2003/99769; (2003); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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.34626-51-2, name is 5-Bromopentan-1-ol, molecular formula is C5H11BrO, molecular weight is 167.0442, as common compound, the synthetic route is as follows.Formula: C5H11BrO

e added pyridine (7.1 g, 90 mmol) and benzoyl chloride (10.2 g, 72.5 mmol) at 0 oC. The resulting mixture was stirred for 3 h at room temperature under nitrogen atmosphere. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with 1% ethyl acetate in petroleum ether to afford 5-bromopentyl benzoate (12.5 g, 77%) as a colorless oil. 1H NMR (400 MHz, CDCl3) d 8.07 (dd, J = 8.4, 1.5 Hz, 2H), 7.62-7.53 (m, 1H), 7.46 (dd, J = 8.4, 7.0 Hz, 2H), 4.36 (t, J = 6.5 Hz, 2H), 3.46 (t, J = 6.7 Hz, 2H), 1.96 (p, J = 7.0 Hz,2H), 1.82 (dt, J = 8.3, 6.5 Hz, 2H), 1.64 (dddd, J = 14.8, 9.5, 6.6, 3.5 Hz, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,34626-51-2, 5-Bromopentan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; KYMERA THERAPEUTICS, INC.; JI, Nan; MAINOLFI, Nello; WEISS, Matthew; (977 pag.)WO2020/10210; (2020); A1;,
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. 59767-24-7, name is 1-(4-Chlorophenyl)-1-phenylethanol. A new synthetic method of this compound is introduced below., Formula: C14H13ClO

(R)-2-[2-[1-(4-Chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine: A mixture of (R)-2-(2-chloroethyl)-1-methyl-pyrrolidine hydrochloride (0.530 g, 2.91 mmol), 1-(4-chlorophenyl)-1-phenylethanol (1.01 g, 4.39 mmol), sodium amide (0.567 g, 14.53 mmol) and toluene (10 mL) was heated at reflux for about 8 hours, cooled to ambient temperature, and filtered. The filtrate was concentrated and the resulting residue was purified by Preparative HPLC on a Kromasil C18 (30×250 mm, 10 mum) column, by eluting with acetonitrile/0.01 M ammonium acetate (3:1) at a flow rate of 42 mL/min. The racemic title compound eluted at 1.57 min. Standard extractive workup with ethyl acetate afforded the racemic title product as an oil (0.360 g, 36%).

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, 59767-24-7, 1-(4-Chlorophenyl)-1-phenylethanol.

Reference:
Patent; AUSPEX PHARMACEUTICALS, INC.; US2009/203763; (2009); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 6850-39-1, 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. 6850-39-1, name is 3-Aminocyclohexanol. A new synthetic method of this compound is introduced below.

Treat a mixture of 3-hydroxycyclohexyl amine (10 g, 86.96 mmol), potassium carbonate (18 g, 130 mmol), ethyl acetate (150 mL) and water (70 mL) with benzyl chloroformate (22.17 g, 130 mmol). Stir the reaction at room temperature for 12 hours. Separate the organic layer, dry the organic over sodium sulfate, filter and concentrate. Add diethyl ether to the residuer. Filter the resulting white precipitate and air dry to afford 19.1 g of the title compound (88%). MS (m/z): 250 (M+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6850-39-1, 3-Aminocyclohexanol, and friends who are interested can also refer to it.

Reference:
Patent; Aicher, Thomas Daniel; Anzeveno, Peter Biagio; Li, Renhua; Krasutsky, Alexei Pavlovych; Mabry, Thomas Edward; Saeed, Ashraf; Snyder, Nancy June; Stephenson, Gregory Alan; Tian, Hongqi; Wallace, Owen Brendan; Winneroski, JR., Leonard Larry; Xu, Yanping; US2009/111800; (2009); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Related Products of 27489-62-9 , The common heterocyclic compound, 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, 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.

In THF (20 mL) were dissolved 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4 -methoxybenzyl)amino)pyrimidine-5-carboxylic acid (180 mg, 0.48 mmol), trans-4-hydroxycyclohexylamine (66 mg, 0.58 mmol) and HATU(220 mg, 0.58 mmol). The solution was cooled in an ice bath and DIEA (0.25 mL, 1.44 mmol) was added then. The reaction was conducted at ambient temperature for 8 h, followed by concentration, addition of water and extraction with ethyl acetate. The organic phase was dried, concentrated and purified by silica gel column chromatography (DCM / methanol = 20 / 1) to give 2-(3-azabicyclo[3.1.0]hexan-3-yl)-4-((3-chloro-4-methoxybenzyl)amino)-N-(trans-4-hydrox ycyclohexanyl)pyrimidine-5-formamide (141 mg, 62 % yield). Molecular formula: C24H30ClN5O3 Molecular weight: 472.0 MS (m/e): 472.0 (M+1) 1H-NMR (400 MHz, CDCl3): delta 8.99 (t, 1H), 8.08 (s, 1H), 7.38 (d, 1H), 7.18 (d, 1H), 6.86 (d, 1H), 5.66 (d, 1H), 4.53 (m, 2H), 3.88(s, 3H), 3.87 (m, 1H), 3.86 (d, 2H), 3.64(m, 1H), 3.50 (d, 2H), 1.29-1.85 (m, 11H), 0.74 (m, 1H), 0.20 (m, 1H).

The synthetic route of 27489-62-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; WANG, Aichen; EP2886540; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 2854-16-2, 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.2854-16-2, name is 1-Amino-2-methylpropan-2-ol, molecular formula is C4H11NO, molecular weight is 89.14, as common compound, the synthetic route is as follows.

5-Chloro-3-(4,4-difluorocyclohexylmethyl)-2-trifluor omethylimidazo[1,2-a]pyridine-7-carboxylic acid (28 mg, 0.093 mmol) obtained in step 3 of Example 61 was dissolved in N,N-dimethylformamide (2.0 mL), and the solution was stirred overnight at room temperature after adding EDC·HCl (36 mg, 0.187 mmol), HOBt·H2O (29 mg, 0.187 mmol), and 1-amino-2-methylpropan-2-ol (17 mg, 0.187 mmol). The mixture was extracted with ethyl acetate after adding a sodium hydrogen carbonate aqueous solution. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (chloroform/methanol=9/1) to give compound 182 (40.4 mg, 85percent). 1H NMR (400 MHz, CDCl3, delta): 7.95 (s, 1H), 7.46 (s, 1H), 6.60 (br s, 1H), 3.49 (d, J = 5.9 Hz, 2H), 3.35 (d, J = 6.9 Hz, 2H), 1.97-1.56 (m, 9H), 1.31 (s, 6H); ESIMS m/z: [M + H]+ 468

The chemical industry reduces the impact on the environment during synthesis 2854-16-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; SAWADA, Takashi; DANJO, Tomohiro; MOTOSAWA, Keiichi; FURUTA, Takayuki; ICHIOKA, Maki; SUGAWARA, Masamori; UESAKA, Noriaki; EP2671582; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 4704-94-3, Adding some certain compound to certain chemical reactions, such as: 4704-94-3, name is 2-(Hydroxymethyl)propane-1,3-diol,molecular formula is C4H10O3, 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 4704-94-3.

Branched malonate molecules 1 and 2 were produced according to the schemes shown in FIGS. 9-10.

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. 4704-94-3, 2-(Hydroxymethyl)propane-1,3-diol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hirsch, Andreas; Beuerle, Florian; Chronakis, Nikos; US2006/47167; (2006); 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. 7287-81-2, name is 1-(m-Tolyl)ethanol, molecular formula is C9H12O, 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. HPLC of Formula: C9H12O

General procedure: To a 20-mL tube equipped with a magnetic stirring bar was added acetophenone 1a (120 mg, 1 mmol), 2 mL of DMSO, iodine (25 mg, 0.1 mmol) and Fe(NO3)3·9H2O (40 mg, 0.1 mmol). Then the tube was sealed after being charged with oxygen to replace the air in it. The tube was placed into a preheated oil bath (130C), and the reaction solution was stirred for 12h. Then the reaction was quenched with water, and the pH of the aqueous phase was adjusted to 11 with 0.1 mol/L NaOH. After being washed with ethyl acetate (3 x 3 mL), the pH of the aqueous phase was adjusted to 2 with 0.1mol/L HCl and extracted with ether (3 x 6 mL). The combined ether phase was dried over anhydrous sodium sulfate and concentrated on a rotary evaporator to obtain the crude product. The crude product was purified by column chromatography on silica gel using ethyl acetate/petroleum ether as eluent to afford 2a as a white solid (104 mg, 85% yield). 1H NMR(600 MHz, DMSO-d6) delta 12.88 (s, 1H), 7.95 (d, J = 7.9 Hz, 2H), 7.62-7.59 (m, 1H), 7.50-7.48 (m, 2H); 13C NMR (125MHz, DMSO-d6) delta 167.3, 132.7, 130.8, 129.2, 128.5.

With the rapid development of chemical substances, we look forward to future research findings about 7287-81-2.

Reference:
Article; Xu, Liang; Chen, Yingying; Shen, Zhenlu; Wang, Yuru; Li, Meichao; Tetrahedron Letters; vol. 59; 49; (2018); p. 4349 – 4354;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts