Alcohols-buliding-blocks

623-04-1, 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 623-04-1 as follows.

Step B; 4-Acetamidobenzyl acetateTo a solution of (4-aminophenyl)methanol (2.0 g, 16.2 mmol) from step A and DMAP (0.40 g, 3.2 mmol)in DCM (50 mL) was added dropwise acetic anhydride (7.6 mL, 81.0 mmol) at 0 0C over 30 min. After stirring under nitrogen for 30 min, the solution was concentrated and extracted with DCM twice. The combined extracts were washed with water and brine, dried over Na2SO4 and concentrated. Column chromatography on silica (20% EA in PE) afforded the title compound as white solid (3.35 g, 100%). 1H NMR (CDCl3, 300 MHz): delta 7.51 (d, J = 8.1 Hz, 2H), 7.31 (d, J = 8.1 Hz, 2H), 5.05 (s, 2H), 2.16 (s, 3H), 2.08 (s, 3H). MS (ESI, Pos. 1.5 kV) m/z 230.0 (M+Na)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,623-04-1, its application will become more common.

Reference:
Patent; SHANGHAI TARGETDRUG CO., LTD.; AVEXA LIMITED; WO2009/89659; (2009); A1;,
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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. 764-48-7, name is Ethylene Glycol Vinyl Ether. This compound has unique chemical properties. The synthetic route is as follows. 764-48-7

General procedure: To a stirred mixture of alcohol, 2-oxo-4-aryl-but-3-enoic acid and DMAP in dichloromethane at 0 C was added dropwise DCC in dichloromethane. After 10 min, the reaction mixture was allowed to warm to room temperature and stirred for 10 h. After filtration of the resulting mixture, solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel using CH2Cl2 as eluant.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,764-48-7, Ethylene Glycol Vinyl Ether, and friends who are interested can also refer to it.

Reference:
Article; Dong, Xiaomei; Wang, Qingxia; Zhang, Qian; Xu, Shuai; Wang, Zhihong; Tetrahedron; vol. 69; 52; (2013); p. 11144 – 11154;,
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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. 558-42-9, name is 1-Chloro-2-methyl-2-propanol. A new synthetic method of this compound is introduced below., 558-42-9

[0309] To a solution of 7-chloro-6-fluoro-lH-pyrazolo[4,3-b]pyridine (300 mg, 1.749 mmol) in DMF (5 mL) was added Cs2C03 (855 mg, 2.62 mmol) and 1 -chloro-2-methylpropan-2-ol (209 mg, 1.924 mmol) and the mixture was heated at 110 ¡ãC for 2 hours. Water (20 mL) was then added and the mixture was extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over Na2S04, filtered, and evaporated to give l-(7-chloro-6-fluoro-2H- pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropan-2-ol and l-(7-chloro-6-fluoro-lH- pyrazolo[4,3-b]pyridin-l-yl)-2-methylpropan-2-ol which were used i without further purification. MS [M+H] found 244.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,558-42-9, 1-Chloro-2-methyl-2-propanol, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KWOK, Lily; LARSON, John David; SABAT, Mark; WO2011/146287; (2011); A1;,
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2854-16-2, 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. 2854-16-2, name is 1-Amino-2-methylpropan-2-ol, molecular formula is C4H11NO, 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.

To a suspension of 2,4,6,8-tetrachloro-pyrimido[5,4-djpyrimidine (1) (3.50 g,i3.Oi mmol) in THF (200 mL) at -78¡ãC, i-amino-2-methyl-propan-2-ol (i.i7 mL, i2.36 mmol) in THF (20 mL) was added via syringe pump (during about 30 mm) followed byDIPEA (2.93 mL, i6.9i mmol) in THF (20 mL). The reaction mixture was stirred at -78¡ãC for additional 30 mi and then allowed to reach the room temperature. Water (250 mL) was added and the resulting suspension was extracted with EtOAc (3 x iOO mL). The combined organic extracts were washed with water (iSO mL), then with brine (iSO mL) and dried over solid anhydrous MgSO4. After filtration, the solvent was removed and the residue waspurified by flash column chromatography using gradient elution from PE/EtOAc (iO:4) toPE/EtOAc (i : i) to give 2-methyl-i -(2,6,8-trichloro-pyrimido[5,4-djpyrimidin-4-ylamino)-propan-2-ol (29)(3.67 g, 92percent yield). 300 MHz ?H NMR (CDC13, ppm): 7.70-7.58 (iH, m)3.70 (2H, d, J=6.i Hz) i.80 (iH, s) i.36 (6H, s). ESI-MS (m/z): 322, 324, 326, 328 [M+Hf?.

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. 2854-16-2, 1-Amino-2-methylpropan-2-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALLEON PHARMACEUTICALS, INC.; DAX, Scott L.; MENCEL, James Joseph; OZOLA, Vita; SUNA, Edgars; SHUBIN, Kirill; (294 pag.)WO2017/3822; (2017); A1;,
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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. 626-18-6, name is 1,3-Benzenedimethanol. This compound has unique chemical properties. The synthetic route is as follows. 626-18-6

To a stirred solution of 1,3-phenylenedimethanol (1.0 g, 7.2 mmol) and imidazole (0.74 g, 11 mmol) in DMF (36 mL) at 0C was added TBDPS-Cl (2.0 mL, 7.6 mmol). After 30 min, the reaction mixture was allowed to warm to rt and stirred for 18h. The mixture was diluted with Et2O, washed with water (4X), then brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography to give 9A (1.2 g, 44 %).1H NMR (500MHz, CDCl3) delta 7.72 (dd, J=8.0, 1.4 Hz, 4H), 7.45 (d, J=7.4 Hz, 2H), 7.43 – 7.37 (m, 4H), 7.34 (d, J=11.8 Hz, 3H), 7.29 (s, 2H), 4.81 (s, 2H), 4.71 (d, J=5.8 Hz, 2H), 1.59 (d, J=11.8 Hz, 1H), 1.13 (s, 9H).

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, 626-18-6, 1,3-Benzenedimethanol.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne M.; KICK, Ellen K.; VALENTE, Meriah Neissel; HU, Carol Hui; HALPERN, Oz Scott; JUSUF, Sutjano; (133 pag.)WO2018/5336; (2018); A1;,
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575-03-1, 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 575-03-1 as follows.

2-(Trimethylsilyl) ethylhydrogen phthalate (1, 1.29 g, 4.83 mmol) [14,15], 7-hydroxy-4-(trifluoromethyl)-coumarin (2, 1.11 g, 4.83 mmol) [16], and4-dimethylaminopyridine (0.65 g, 5.3 mmol) were dissolved in amixture of anhydrous methylene chloride (15 mL) and anhydrous DMF (9 mL). N,N-Dicyclohexylcarbodiimide was quickly added tothe reaction mixture, which was stirred under N2 overnight. Dicyclohexyl urea was filtered off, and the filtrate was diluted in10 mL of methylene chloride. The solution was washed with brineand then dried over anhydrous Na2SO4. The crude product wascollected by evaporation under reduced pressure and then purifiedby flash chromatography on silica gel (PE/EA = 30:1) to yield 3(0.92 g, 45percent) as a white solid. Compounds 3 were characterized by1H NMR, 13C NMR and ESI-HRMS analyses (Figs. S3?S5 inSupporting information). 1H NMR (500 MHz, CDCl3): d 7.93?7.87(m, 1H), 7.87?7.78 (m, 2H), 7.69?7.62 (m, 2H), 7.45 (d, 1H,J = 2.5 Hz), 7.38 (dd, 1H, J = 9.0, 2.5 Hz), 6.80 (s, 1H), 4.46?4.37 (m,2H), 1.12?1.08 (m, 2H), 0.05 (s, 9H); 13C NMR (100 MHz, CDCl3): d166.71, 165.75, 158.51, 155.11, 154.29, 131.84, 131.69, 131.56,131.39, 129.37, 128.96, 126.35, 118.99, 111.10, 64.40, 17.37,1.53; ESI-HRMS (m/z): Calcd. for [C23H21F3O6Si + Na] 501.09572([M + Na]+), found 501.09485.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,575-03-1, its application will become more common.

Reference:
Article; Wang, Xin-Yu; Guan, Feng-Jie; Li, Bin; Zhang, Hua; Wu, Hong-Wei; Ji, Kai; Liu, Chuan-Xiang; Chinese Chemical Letters; vol. 27; 2; (2016); p. 211 – 214;,
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Adding a certain compound to certain chemical reactions, such as: 4654-39-1, 2-(4-Bromophenyl)ethanol, 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, 4654-39-1, blongs to alcohols-buliding-blocks compound. 4654-39-1

Bis(pinacolato)diboron (7.58 g, 29.85 mmol), potassium acetate (7.32 g, 74.58 mmol), Pd(dppf)Cl2 (50 mg) and 4-Bromophenethyl alcohol (5 g, 24.8 mmol) were dissolved in dry dioxane under nitrogen. After stirring at 100 C for 24 h, the mixture was transferred to a separatory funnel, extracted with dichloromethane (DCM) and then washed with brine and dried with anhydrous magnesium sulfate. The crude product was purified by silica gel column chromatography with a mixture of petroleum ether (PE): ethyl acetate (EA) = 4:1 as eluent to obtain the pure product 4.63 g (yield, 75%). 1H NMR (600 MHz, CDCl3): 2.84(1.9H, t, J=6.78 Hz), 3.79 (1.9H, t, J=6.78 Hz), 7.21 (1.9H, d, J=7.76 Hz), 7.75 (1.8H, d, J=7.76 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 4654-39-1.

Reference:
Article; Liu, Jikang; Jiang, Pengfei; Wang, Yao; Tu, Guoli; Chinese Chemical Letters; (2019);,
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2615-15-8, 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 2615-15-8 as follows.

(a) 1,17-Diazido-3,6,9,12,15-pentaoxaheptadecane A solution of dry hexaethylene glycol (25 g, 88 mmol) and methanesulfonyl chloride (22.3 g, 195 mmol) in dry THF (125 mL) was kept under argon and cooled to 0 C. in an ice/water bath. A solution of triethylamine (19.7 g, 195 mmol) in dry THF (25 mL) was added dropwise over 45 min. After 1 hr the cooling bath was removed and the reaction was stirred for another for 4 hrs. Water (55 mL) was then added to the mixture, followed by sodium hydrogencarbonate (5.3 g, to pH 8) and sodium azide (12.7 g, 195 mmol). THF was removed by distillation and the aqueous solution was refluxed for 24 h (two layers were formed). The mixture was cooled, ether (100 mL) was added and the aqueous phase was saturated with sodium chloride. The phases were separated and the aqueous phase was extracted with ether (4*50 mL). The combined organic phases were washed with brine (2*50 mL) and dried (MgSO4). Filtration and evaporation of the solvent gave a yellow oil 26 g (89%). The product was used in the next step without further purification.

The chemical industry reduces the impact on the environment during synthesis 2615-15-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GE HEALTHCARE LIMITED; BARNETT, DAVID JONATHAN; HENRIKSEN, INGRID; CONSTANTINOU, MARIA; PETTITT, ROGER PAUL; US2013/209358; (2013); A1;,
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2050-25-1, Adding a certain compound to certain chemical reactions, such as: 2050-25-1, 2-(2-(Benzyloxy)ethoxy)ethanol, 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, 2050-25-1, blongs to alcohols-buliding-blocks compound.

Step A; 2-[2-(2-Benzyloxyethoxy)ethoxy]benzonitrile; [Show Image] [Show Image] 2-Hydroxybenzonitrile (300 mg, 2.52 mmol), di(ethylene glycol) benzyl ether (593 mg, 3.02 mmol), and 1,1′-azobis(N,N-dimethylformamide) (867 mg, 5.04 mmol) were dissolved in toluene (15 ml). Thereafter, tri-n-butylphosphine (1.26 ml, 5.04 mmol) was added at 20C to the obtained solution, and the obtained mixture was stirred at the same above temperature for 2 hours. The generated precipitate was filtrated, and the filtrate was then diluted with ethyl acetate (20 ml). The ethyl acetate solution was washed with water twice, and then with a saturated saline solution once. The resultant was dried over anhydrous sodium sulfate, and was then concentrated under reduced pressure. The obtained pale brown oil product was purified by silica gel column chromatography (dichloromethane), so as to obtain 2-[2-(2-benzyloxyethoxy)ethoxy]benzonitrile (529 mg, 71%) in the form of a colorless oil product. 1H-NMR (400MHz, CDCl3) delta (ppm): 3.65-3.67 (2H, m), 3.79-3.81 (2H, m), 3.93 (2H, t, J=5.0Hz), 4.24 (2H, t, J=5.0Hz), 4.57 (2H, s), 6.88 (1H, d, J=7.5Hz), 6.99 (1H, t, J=7.5Hz), 7.26-7.35 (5H, m), 7.49 (1H, t, J=7.5Hz), 7.54 (1H, d, J=7.5Hz) ESI (LC-MS positive mode) m/z 298 (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,2050-25-1, its application will become more common.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1854792; (2007); A1;,
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105-30-6, 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.105-30-6, name is 2-Methylpentan-1-ol, molecular formula is C6H14O, molecular weight is 102.18, as common compound, the synthetic route is as follows.

General procedure: Isonicotinic acid (1a) or nicotinic acid (1b, 3.08 g, 0.025 mol) and thionyl chloride (20.5 g, 0.17mol, 12.5mL) were stirred at reflux for 2 h (the end of SO2 evolution). Excess of thionyl chloride was distilled off under normal pressure, and then under reduced pressure. To the residue (white precipitate) methylene chloride (50mL) was added. The solution of the appropriate 2-metylalkyl alcohol (0.025mol) in methylene chloride (10 mL) was added dropwise. The reaction was stirred for 2 h at reflux to complete the evolution of hydrogen chloride. The reaction mixture was adjusted to pH 12 with aqueous potassium carbonate. After layers were separated, the organic layer was dried over anhydrous calcium chloride. Evaporation of the solvent gave a crude product. Purity of 4a, 4b, 5a, 5b was satisfactory (TLC). 4c, 4d, 5c, 5d were purified by column chromatography.

Statistics shows that 105-30-6 is playing an increasingly important role. we look forward to future research findings about 2-Methylpentan-1-ol.

Reference:
Article; Huras, Bogumi?a; Zakrzewski, Jerzy; Krawczyk, Maria; Bombi?ska, Danuta; Cieniecka-Ros?onkiewicz, Anna; Michalczyk, Alicja; Medicinal Chemistry Research; vol. 26; 3; (2017); p. 509 – 517;,
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