Month: August 2021

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1467-84-1, name is (trans-4-Aminocyclohexyl)methanol, the common compound, a new synthetic route is introduced below. category: alcohols-buliding-blocks

PREPARATION 50 2-((1r,4r)-4-Aminocyclohexyl)acetonitrile a) tert-Butyl (1 r,4r)-4-(hydroxymethyl)cyclohexylcarbamate Di-tert-butyl dicarbonate (3.04 g, 13.9 mmol) was added to a stirred solution of ((1r,4r)-4-aminocyclohexyl)methanol (1.50 g, 11.6 mmol) in tetrahydrofuran (20 mL). After stirring overnight at room temperature, the mixture was evaporated and partitioned between ethyl acetate and water. The organic layer was washed with water, brine, dried (MgSO4) and evaporated. The residue was treated with hexanes and the suspension was filtered to give the title compound (2.11 g, 79%) as a white solid. LRMS (m/z): 228 (M-H)+.1H NMR (300 MHz, DMSO-d6) delta ppm 0.84 – 0.95 (m, 2H), 1.05 – 1.18 (m, 2H), 1.20 – 1.29 (m, 2H), 1.40 (s, 9H), 1.71 -1.80 (m, 3H), 3.14 (m, 1H), 3.21 (t, 2H), 4.41 (t, 1H), 6.73 (d, 1H).

The synthetic route of 1467-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2011/157397; (2011); A1;,
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Application of 2050-25-1, 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. 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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.

26.3 g of diethylene glycol benzyl ether was dissolved in 140 mL of DMF, 5.4 g of 60% NaH was added at 0 to 5 C., and the mixture was stirred for 30 minutes. Then, a solution of 17.3 g of 3-nitrophthalonitrile in 60 mL of DMF was added dropwise and the mixture was stirred at 0 to 5 C. for 2 hours. The reaction solution was discharged into 2500 mL of diluted hydrochloric acid, stirred for 30 minutes, and the precipitate was collected by filtration, washed with water and dried. The obtained solid was recrystallized from 80% isopropyl alcohol aqueous solution to obtain a yellowish white solid 21.7 g (melting point 98.5 to 100.5 C) was obtained.

According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YAMAMOTO CHEMICALS INCORPORATED; KUMAGAE, YOJIRO; HORIUCHI, KENICHIRO; (40 pag.)JP2016/204536; (2016); A;,
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Related Products of 2919-23-5 ,Some common heterocyclic compound, 2919-23-5, 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 suspension of sodium hydride (2 equiv, 60% in mineral oil) in dry THF (0.44 M) under nitrogen atmosphere was added a solution of cyclobutanol (1.05 equiv) in dry THF (1.4 M) at 0 C. The reaction mixture was stirred at room temperature for 30 minutes before 2,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)-methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv) in dry THF (0.33 M) was added and the resulting reaction mixture was stirred at 30 C. for 1 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution. The organic solvent was removed under reduced pressure and the resulting aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure. The crude obtained was purified by flash column chromatography on silica gel (5% ethyl acetate in petroleum ether) to afford the title compound (95% yield) as a white solid. MS (ESI) m/z 479.2 [M+1]+.

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. 2919-23-5, Cyclobutanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Signal Pharmaceutical LLC; Calabrese, Andrew Antony; Jeffy, Brandon; Robinson, Dale; Zhu, Dan; Huang, Dehua; Elsner, Jan; Boylan, John; Tehrani, Lida; Nagy, Mark A.; Moghaddam, Mehran Fallah; Raheja, Raj Kumar; Erdman, Paul; Narla, Rama K.; Harris, Roy L.; Tran, Tam Minh; Riggs, Jennifer; Ning, Yuhong; US2014/200206; (2014); A1;,
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Reference of 637031-88-0, 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 637031-88-0, name is 3,3-Difluorocyclobutanol. This compound has unique chemical properties. The synthetic route is as follows.

[0433] Step D: Preparation of 6-fluoro-l-(trifluoromethyl)-5,6- dihvdrospirorcvclopentarc1pyridine-7,2′-rL31dioxolan1-4-ol and l-(trifluoromethyl)-5,6- dihvdrospirorcvclopentarc1pyridine-7,2′-rL31dioxolan1-4-ol: A solution of 4′-bromo-6′-fluoro- -(trifluoromethyl)spiro[l,3-dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine] (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 1,4-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 muEpsilon, 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 muEpsilon, 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- dihvdrospirorcvclopentarclpyridine-7.2′-ri.31dioxolanl-4-ol: LCMS ESI (+) (M+H) m/z 280. Data for l-(trifluoromethyl)-5,6-dihydrospiro[cyclopenta[clpyridine-7,2′-[L31dioxolanl-4-ol: LCMS ESI (+) (M+H) m/z 262. [0434] Step E: Preparation of 4-(3,3-difluorocvclobutoxy)-6-fluoro-l-(trifluoromethyl)- 5,6-dihydrospiro[cyclopenta[clpyridine-7,2′-[L31dioxolanel and 4-(3 , 3 -difluorocy clobutoxy)- 1 – (trifluoromethyl)-5,6-dihvdrospirorcvclopentarc1pyridine-7,2′-rL31dioxolane1: A solution of impure 6′-fluoro- -(trifluoromethyl)spiro[l,3-dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine]- 4′-ol (44.0 mg, 0.16 mmol), polymer supported 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 azodicarboxylate (120 mu^, 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% EtOAc/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 -difluorocvclobutoxy)-6-fluoro- 1 – (trifluoromethyl)-5,6-dihvdrospirorcvclopentarc1pyridine-7,2′-rL31dioxolane1: LCMS ESI (+) (M+H) m/z 370. Data for 4-(3.3-difluorocvclobutoxyVl-(trifluoromethvn-5.6- dihvdrospirolcvclopentalc1pyridine-7.2′-r 1.3 ldioxolanel : LCMS ESI (+) (M+H) m/z 352.

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 637031-88-0, 3,3-Difluorocyclobutanol.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; WEHN, Paul; XU, Rui; YANG, Hanbiao; (146 pag.)WO2016/144826; (2016); A1;,
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Synthetic Route of 869725-53-1, 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. 869725-53-1, name is 2-Bromo-5-(trifluoromethyl)benzyl Alcohol, molecular formula is C8H6BrF3O, 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.

Preparation 3 1-Bromo-2-(bromomethyl)-4-(trifluoromethyl)benzene To a solution of (2-bromo-5-(trifluoromethyl)phenyl)methanol (4.7 g, 18 mmol) in methylene chloride (50 mL) at -10 C. was added carbon tetrabromide (CBr4) (7.17 g, 21.6 mmol). The resulting mixture was stirred at -10 C. for 15 minutes. Triphenylphosphine (5.61 g, 21.4 mmol) was then slowly added portionwise. This mixture was stirred at room temperature for 16 hours. The mixture was partitioned between saturated ammonium chloride (NH4Cl) (50 ml) and methylene chloride (2*50 mL). The combined organic layers were washed with saturated NaCl (50 mL), dried (MgSO4) and concentrated. The residue was purified by flash chromatography (silica gel) (eluted with 3:1 hexanes-ethyl acetate) to yield the title compound as a white solid (4.01 g). 1H NMR (400 MHz, CDCl3) delta 4.6 (s, 2H) 7.5 (dd, J=8.3, 1.6 Hz, 1H) 7.8 (m, 2H).

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 869725-53-1, 2-Bromo-5-(trifluoromethyl)benzyl Alcohol.

Reference:
Patent; Pfizer Inc; US2007/213371; (2007); A1;,
Alcohol – Wikipedia,
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Related Products of 4249-72-3 ,Some common heterocyclic compound, 4249-72-3, molecular formula is C14H14O2, 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.

The reaction feed is carried out in a glove box.Weigh lignin dimer 5 (0.1 mmol, 21.4 mg),Photocatalyst antimony trichloride (1 mol%), auxiliary tetrabutylammonium chloride (5 mol%),Di-tert-butyl azodicarboxylate (0.1 mmol) and 0.5 mL of acetonitrile were placed in a 10 ml reaction pressure tube. The reaction pressure tube is sealed in a blue light at 420 nm.After stirring for 12 hours, after the lignin dimer 5 is completely converted,Continue to add lignin dimer 5 (0.1 mmol, 21.4 mg) to the reaction.And di-tert-butyl azodicarboxylate (0.1 mmol), each time after the reaction,The conversion and product yield are shown in Figure 3. After the tenth feeding reaction is over,After separation by silica gel column chromatography (ethyl acetate: petroleum ether = 1:5, volume ratio), the product benzaldehyde (84.8 mg, yield 80%)And 1-(phenoxymethyl)-1,2-dicarboxylic acid di-tert-butyl ester-oxime (1)(267.0 mg, yield 79%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4249-72-3, its application will become more common.

Reference:
Patent; Jilin University; Zhang Yuetao; He Jianghua; Wang Yinling; (11 pag.)CN110156581; (2019); A;,
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Synthetic Route of 2566-44-1 ,Some common heterocyclic compound, 2566-44-1, molecular formula is C5H10O, 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 2-cyclopropylethanol at 0 C. (0.98 g, 11 mmol) and pyridine (2.4 mL, 30 mmol) in DCM (15 mL) was added 4-methylbenzene-1-sulfonyl chloride (22 g, 11 mmol). The cold bath was removed and the mixture allowed to warm to room temperature for 14 h. The reaction mixture was diluted with water and Et2O and the phases were separated. The organic phase was washed sequentially with water, 10% aqueous HCl and brine, dried (MgSO4) filtered and concentrated under reduced pressure to give Compound 4a (2.0 g, 74%) as a clear colorless oil. Compound 4a was used in the next step without further purification. MS m/z=241.4 (M+H). 1H NMR (400 MHz, chloroform-d) delta 7.77 (d, J=8.1 Hz, 2H), 7.32 (d, J=8.4 Hz, 2H), 4.06 (t, J=6.7 Hz, 2H), 2.42 (s, 3H), 1.56-1.45 (m, 2H), 0.70-0.57 (m, 1H), 0.44-0.32 (m, 2H), 0.04-0.10 (m, 2H).

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. 2566-44-1, 2-Cyclopropylethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Pi, Zulan; Bilder, Donna M.; Brigance, Robert Paul; Finlay, Heather; Jiang, Wen; Johnson, James A.; Lawrence, R. Michael; Meng, Wei; Myers, Michael C.; Phillips, Monique; Tora, George O.; Zhang, Xiaojun; (59 pag.)US2017/275272; (2017); A1;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 927-74-2, 3-Butyn-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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

(But-3-yn- 1 -yloxy) (tert-butyl)dimethylsilane (3.5) [00139] Compound 3.5 was synthesised using a similar procedure by Nadeau et al. To a solution of 3-butyn-1 -ol (3.00 g, 42.8 mmol) in dichloromethane (60 mL) was added imidazole (7.28 g, 107 mmol) and cooled to 5 C. tert-Butyldimethylsilyl chloride (6.45 g, 42.8 mmol) was added and the reaction mixture was stirred at 25 C for 1 6 hours. Dichloromethane (100 mL) was added and the mixture was washed with water (2 x 50 mL) and brine (50 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to afford compound 3.5 (7.73 g, 98%) as a colourless oil. 3.5: C10H20OSi (Mr 184.35); 1H NMR (400 MHz, CDCI3) O (ppm) 3.74 (t, J=7.1 Hz, 2H), 2.40 (td, J= 7.1, 2.7 Hz, 2H), 1 .95 (t, J= 2.7 Hz, 1 H), 0.90 (5, 9H),0.07 (5, 6H); 13C NMR (101 MHz, CDCI3) O (ppm) 81.6, 69.4, 61.9, 26.0, 23.0,18.4, -5.2. Does not ionise in ESI-MS. Nb. 1H NMR was consistent with literature data.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,927-74-2, 3-Butyn-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; WANG, Bing, Hui; KRUM, Henry; SCAMMELLS, Peter; VINH, Natalie; SIMPSON, Jamie; CHALMERS, David; (148 pag.)WO2016/29263; (2016); A1;,
Alcohol – Wikipedia,
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Application of 6351-10-6, 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. 6351-10-6, name is 2,3-Dihydro-1H-inden-1-ol. A new synthetic method of this compound is introduced below.

General procedure: A mixture of alcohol 1a (100 mg, 0.54 mmol), alkene 2a (43 mg, 0.54 mmol), Ca(OTf)2 (18.3 mg, 0.05 mmol),Bu4NPF6 (21 mg, 0.05 mmol) was heated under solvent free condition at 70C for 1.5 h until complete consumption of the starting material as monitored by TLC. After the completion of the reaction the mixture was purified by flash column chromatography (petroleum ether) to afford the desired product 3a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6351-10-6, its application will become more common.

Reference:
Article; Yaragorla, Srinivasarao; Pareek, Abhishek; Dada, Ravikrishna; Almansour, Abdulrahman I.; Arumugam, Natarajan; Tetrahedron Letters; vol. 57; 52; (2016); p. 5841 – 5845;,
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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. 3513-81-3, name is 2-Methylenepropane-1,3-diol. A new synthetic method of this compound is introduced below., Formula: C4H8O2

Preparation 3 3-Octadecylaminocarbonyloxy-2-methylenepropan-1-ol Octadecyl isocyanate (59.1 g) and 2-methylene-propane-1,3-diol (17.7 g) were dissolved and stirred in pyridine (100 ml) for 24 hours at 22°C. Water (200 ml) was added, and the mixture was extracted with chloroform (3 * 200 ml). The chloroform extracts were washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo . The mixture was purified through a column of silica gel 60 (70-230 mesh, 100 g) eluding with chloroform/ether 1: 1. Further purification was achieved by chromatography on a Waters PrepLC.(R)./System 500A using a PrepPAK.(R).-500/SILICA cartridge with chloroform/ether/pentane 1: 1: 3 as eluent. The product was recrystallized from acetone. Mp. 71-73°C. Elemental analysis: calculated C 71.99percent, H 11.82percent, N 3.65percent, found C 71.93percent, H 11.93percent, N 3.64percent.

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, 3513-81-3, 2-Methylenepropane-1,3-diol.

Reference:
Patent; LEO PHARMACEUTICAL PRODUCTS LTD. A/S, (LOVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB); EP247201; (1991); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts