Ethers-buliding-blocks

The chemical industry reduces the impact on the environment during synthesis 6346-09-4, name is 4,4-Diethoxybutan-1-amine, I believe this compound will play a more active role in future production and life. 6346-09-4

To a solution of commercially available 4-aminobutyaldehyde diethyl acetal (21)[1] (5.00 g, 31.0 mmol) in THF (75 mL) was added TEA (6.50 mL, 4.70 g, 46.5 mmol) at 0-5 C (ice-bath temperature). The mixture was allowed to stir for 5 min, and treated with a solution of Boc2O (6.76 g, 31.0 mmol) in THF (30 mL) drop-wise. The reaction mixture was stirred at 0-5 C for 30 min and allowed to warm to RT.and stir for 3 h. The mixture was transferred to a separatory funnel and partitioned with H2O (100 mL) and EtOAc (200 mL). The organic layer was separated, dried (anhydrous Na2SO4), filtered and concentrated to afford 7.71 g (95% yield) of compound 22 as a viscous slightly yellow oil: 1H NMR (400 MHz,CDCl3) delta 4.63 (bs, 1H), 4.46 (t, J = 5.39 Hz, 1H), 3.55 (ABq of q, J = 9.32, 7.14 Hz, Dn = 62.10 Hz, 4H), 3.12 (q, J = 6.40 Hz, 2H), 1.65 – 1.60 (m, 2H), 1.57 – 1.50 (m, 2H), 1.42 (s, 9H), 1.18 (t, J = 6.90 Hz, 3H). 13C NMR (100 MHz, DMSO-d6) delta 156.10, 102.47, 77.83, 60.99, (BocNHCH2- obscured by DMSO solvent peak ), 31.18, 28.78, 25.36, 15.83. HRMS ESI-TOF (m/z) = 284.1814 (284.1832 calculated for C13H27NO4Na) [M+Na].

The chemical industry reduces the impact on the environment during synthesis 6346-09-4. I believe this compound will play a more active role in future production and life.

Reference:
Article; Omran, Anahid; Eslamimehr, Shakiba; Crider, A. Michael; Neumann, William L.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1897 – 1902;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

103-50-4, 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. 103-50-4 name is Benzyl ether, This 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.

General procedure: To a sealed tube containing the respective azobenzene 1 (0.25 mmol), dibenzyl ether 2 (0.75 mmol), Pd(OAc)2 (0.025 mmol), and DCE/AcOH (1:1, v/v, 1 mL in all) was added TBHP (1.5 mmol). After stirring vigorously at 60 C for 12 h, the mixture was evaporated under vacuum. The corresponding product 3 was isolated by silica gel column chromatography with a PE/EtOAc mixture as eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Benzyl ether, and friends who are interested can also refer to it.

Reference:
Article; Hong, Gang; Aruma, Alfred Njasotapher; Zhu, Xiaoyan; Wu, Shengying; Wang, Limin; Synthesis; vol. 48; 8; (2016); p. 1147 – 1158;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 35896-58-3

2,3,4,5-Tetramethoxytoluene 3 (2.1 g, 10 mmol) and NaBr (1.1 g, 10 mmol) were dissolved in AcOH (5 mL), a solution of 30% H2O2 (1.2 mL, 10 mmol) was added dropwise over 5 min at room temperature. The mixture was stirred and heated at 40 C for 1 h and quenched with H2O( 5 mL) and extracted with diethyl ether (3 ¡Á 30 mL). The combined organic phases were washed with saturated NaHCO3(3 ¡Á 10 mL) until pH 7, then dried over anhydrous Na2SO4,and evaporated under reduced pressure to give yellow oil 4 (2.9 g) in quantatitive yield. 1H NMR (400 MHz, CDCl3) delta 3.92 (s, 3H, OCH3), 3.91(s, 3H, OCH3), 3.85 (s, 3H, OCH3), 3.79 (s, 3H, OCH3),2.30 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3)delta 148.3, 147.2, 146.3,145.5, 127.3, 114.3, 61.4 (OCH3), 61.1 (OCH3), 60.9(OCH3), 60.8 (OCH3), 15.9 (CH3). GC-MS (EI): m/z = 290.

Statistics shows that 35896-58-3 is playing an increasingly important role. we look forward to future research findings about 1,2,3,4-Tetramethoxy-5-methylbenzene.

Reference:
Article; Qiu, Yong-Fu; Lu, Bin; Yan, Yi-Yu; Luo, Wan-Yue; Wang, Jin; Hu, Xiao; Chemical Papers; vol. 73; 11; (2019); p. 2745 – 2748;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

321-28-8, Adding some certain compound to certain chemical reactions, such as: 321-28-8, name is 1-Fluoro-2-methoxybenzene, 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 321-28-8.

Step 1: Preparation of 3′-fluoro-4′-methoxy-acetophenone. acetyl chloride (51.0 g, 0.65 mol) was added dropwise to a stirred solution of aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 ML), maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C. before the dropwise addition of 2-fluoroanisole (62.6 g, 0.5 mol).. The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L).. The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 ML).. The combined organic layers were washed with water (2*150 ML), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 ML. Hexanes were added and a white solid formed which was isolated by filtration and air dried.. This material was recrystallized from a mixture of dichloromethane and hexanes to afford (77.2 g, 92%) of material suitable for use in the next step: mp 92-94 C.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 321-28-8.

Reference:
Patent; G. D. Searle & Co.; US6342510; (2002); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

5111-65-9,Some common heterocyclic compound, 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, molecular formula is C11H9BrO, 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 21.2: 6-methoxy-naphthalen-2-ylamine A solution of 2-bromo-6-methoxy-naphthalene (237 mg, 1 mmol), Pd (dba)2 mg, 0.05 mmol), tri-t-buthylphosphonium tetrafluoroborate (14 mg, 0.05 mmol), and lithium bis (trimethylsilyl)amide (1 M in hexane, 1.1 mL, 1.1 mmol) is stirred in toluene (2.5 mL) under argon for 6 h. The reaction mixture is taken in diethyl ether (20 mL), and quenched with 1 M HCI. The organic phase is extracted with water, the combined aqueous phases are treated with 1 M sodium hydroxide and extracted with DCM. The combined organic phases are dried over magnesium sulfate, the solvent is evaporated in vacuo and the residue is purified by column flash chromatography on silica gel (ethyl acetate) to afford 6-methoxy- naphthalen-2-ylamine (110 mg, 64 %), HPLC tR : 3.07, (M+H) + = 173.9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-6-methoxynaphthalene, its application will become more common.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/97135; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DE LA ROSA, Martha Alicia; KAZMIERSKI, Wieslaw Mieczyslaw; WASHIO, Yoshiaki; (112 pag.)WO2019/3141; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

5961-59-1, The chemical industry reduces the impact on the environment during synthesis 5961-59-1, name is 4-Methoxy-N-methylaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 2,4-Dichloropyrimidine (1) (0.149g, 1.0 mmol) in 15 mL isopropanol was added 4-methoxy-N-methylaniline derivative (2) (1.0 mmol). The reaction mixture was stirred at room temperature and monitored by TLC. When the reaction was completed, the solvent was removed under vacuum and the slurry was dilute with water (10 mL). The solution was adjusted to pH 9 with a saturated NaHCO3 solution, extracted with ethyl acetate (10 mL¡Á3) for three times, the organic phase was washed with water (10 mL), dried over sodium sulfate, concentrated and purified by column chromatography to give the target compound 3a-3b. 2-Chloro-N-(4-methoxyphenyl)-N-methylpyrimidin-4-amine (3a) White solid. Yield: 79percent. 1H NMR (400 MHz, Chloroform-d) delta 7.85 (d, J = 6.1 Hz, 1H), 7.14 (d, J = 2.2 Hz, 1H), 7.12 (d, J = 2.3 Hz, 1H), 6.99 (d, J = 2.3 Hz, 1H), 6.97 (d, J = 2.2 Hz, 1H), 6.08 (d, J = 6.1 Hz, 1H), 3.85 (s, 3H), 3.44 (s, 3H). 13C NMR (101 MHz, CDCl3) delta 163.86, 160.66, 158.97, 155.98, 136.25, 128.03, 115.50, 103.27, 55.55, 38.35. HRMS (ESI) (m /z) [M+H]+ calcd for C12H12N3OCl, 250.0742; found, 250.0725. Purity: 100.0percent (by HPLC).

The chemical industry reduces the impact on the environment during synthesis 4-Methoxy-N-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Xu, Shaoyu; An, Baijiao; Li, Yuxin; Luo, Xunbang; Li, Xingshu; Jia, Xian; Bioorganic and Medicinal Chemistry Letters; vol. 28; 10; (2018); p. 1769 – 1775;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1535-75-7, 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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

According to Scheme 8, hydroxylamine sulfate (18 g, 3 equivalents) was dissolved in water (80 mL) and then chloral hydrate (7.3 g, 1.2 equivalents) was added. After 15 min, a solution of the starting aniline (5.0 mL, 37 mmol), dissolved in 1 N HCl (44 mL, 1.2 equivalents), was added dropwise (20 min) to the reaction mixture. The resulting cloudy mixture was heated at 80 C. for 1 h, cooled to rt, and diluted with CHCl3 (160 mL). The aqueous layer was extracted with CHCl3 (2¡Á80 mL). The combined organic layers were dried (Na2SO4), filtered and evaporated. Hexanes (40 mL) were added. Evaporation of the solvent provided crude product which was used in the next step without further purification: MS(ESI): 247 (M-H)-.

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.

Reference:
Patent; Icagen, Inc.; US2005/59823; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1484-26-0, These common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, 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: To a solution of amine (1 mmol) in 3 mL of pyridine at 0¡ãC was slowly added the appropriate benzenesulfonyl chloride (1.1 mmol, 1.1 equiv). The mixture was stirred for 12 h at 25¡ãC. The mixture was quenched with 2N HCl, extracted with EtOAc, dried over anhydrous MgSO4, and concentrated in vacuum. The crude product was purified by recrystallization and/or chromatography as noted below.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1484-26-0.

Reference:
Article; Kril, Liliia M.; Vilchez, Valery; Jiang, Jieyun; Turcios, Lilia; Chen, Changguo; Sviripa, Vitaliy M.; Zhang, Wen; Liu, Chunming; Spear, Brett; Watt, David S.; Gedaly, Roberto; Bioorganic and Medicinal Chemistry Letters; vol. 25; 18; (2015); p. 3897 – 3899;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 2930-05-4, name is 2-((Benzyloxy)methyl)oxirane, This compound has unique chemical properties. The synthetic route is as follows., 2930-05-4

General procedure: To a mixture of epoxide (1 equiv) and NaN3 (1.5 equiv) in CH3CN-H2O (8:2, 10 mL) Montmorillonite K 10 (5% w/w) was added. The reaction mixture was stirred at 80C for a specified time as required to complete the reaction. After completion as indicated by TLC, the reaction mixture was then filtered, the filter pad was washed with CH3CN and the combined filtrates were evaporated. The reaction mixture was extracted with EtOAc, the combined organic layers were washed with H2O and brine, dried over anhydrous Na2SO4, and evaporated under reduced pressure. The crude product was then purified by column chromatography over silica gel using EtOAc/petroleum ether as eluent to provide the pure azido alcohol. Characterization data of all the products are shown below.

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.

Reference:
Article; Ch Ghosh, Keshab; Banerjee, Isita; Sinha, Surajit; Synthetic Communications; vol. 48; 22; (2018); p. 2923 – 2934;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem