Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 101597-25-5, 1,1-Bis(4-methoxyphenyl)prop-2-yn-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, HPLC of Formula: C17H16O3, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C17H16O3

General procedure: A solution of the naphthol (1 mol equiv) and the appropriate 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol (1 mol equiv), in the presence of pyridinium p-toluenesulfonate (PPTS) (5 mole %) and trimethyl orthoformate (2 mol equiv) in 1,2-dichloroethane (150 mL),was heated under reflux for up to 4 h (the reaction time being determined by TLC examination of the reaction mixture). The cooled solvent was removed under vacuum to afford the crude product, which was either purified by flash column chromatography or by crystallisation. The following compounds were obtained in this manner: 4.8.1. 3-Benzoyl-6,6-bis(4-methoxyphenyl)-6H-benzo[h]furo[3,2-f]chromene 9. 3-Benzoyl-6,6-bis(4-methoxyphenyl)-6H-benzo[h]furo[3,2-f]chromene 9 from 7 and 8 as pale pink microcrystals after crystallisation from EtOAc and hexane, 52.4%, mp 188 – 190C; upsilonmax 2831, 1651, 1606, 1506, 1351, 1236, 1173, 1028, 1017, 876, 836, 726, 706, 683, 663, 646 cm-1; deltaH (CDCl3) 3.76 (6H, s, OMe), 6.13 (1H, d, J9.9 Hz, 5-H), 6.82 e6.85 (4H, m, AreH), 7.44 e7.47 (4H, m, AreH),7.51 e7.65 (6H, m, AreH, 4-H), 7.93 e7.95 (2H, m, Ar eH), 8.02 (1H, s,2-H), 8.19 (1H, d, J 7.8 Hz, Ar eH), 8.45 (1H, d, J 8.1 Hz, AreH); deltaC(CDCl3) 55.22, 82.22, 110.56, 113.38, 117.80, 119.99, 121.17, 122.83,123.08, 123.64, 124.09, 125.90, 127.09, 127.11, 128.28, 128.62, 129.67,132.92, 137.34, 139.29, 145.27, 147.04, 151.68, 158.84, 190.48 (Found M+H+, 539.1844; C36H26O5 requires M+H+, 539.1853).

The synthetic route of 101597-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aiken, Stuart; Allsopp, Ben; Booth, Kathryn; Gabbutt, Christopher D.; Heron, B. Mark; Rice, Craig R.; Tetrahedron; vol. 70; 49; (2014); p. 9352 – 9358;,
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Application of 37585-16-3, 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 37585-16-3, name is (2-Amino-4-chlorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Benzyl alcohol derivative 11 (1 eq.) was dissolved in CH2Cl2 (0.4 M). Manganese (IV) oxide (2.1 eq.)was added under argon and the solution was left to stir at room temperature for 48 h. The progress ofthe reaction was monitored by TLC analysis. After completion, manganese oxide was filtered off andthe resulting filtrate was concentrated under reduced pressure. The crude product was purified by silicacolumn chromatography employing mixtures of n-hexane and ethyl acetate as eluents to obtain thedesired product 10.

According to the analysis of related databases, 37585-16-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jarrige, Lucie; Merad, Jeremy; Zaied, Siwar; Blanchard, Florent; Masson, Geraldine; Synlett; vol. 28; 14; (2017); p. 1724 – 1728;,
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Adding a certain compound to certain chemical reactions, such as: 23377-40-4, 3-(Hexadecyloxy)propan-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, COA of Formula: C19H40O2, blongs to alcohols-buliding-blocks compound. COA of Formula: C19H40O2

Example 6 Hexadecyloxypropyl-2′,3′-isopropylideneuridin-5′-yl-vinyphosphonate TPSCl (5.54 g, 18.3 mmol) is added to the mixture of vinylphosphonic acid from the example 1 (1.8 g, 6.1 mmol), hexadecyloxypropanol (1.45 g, 3.05 mmol), and 1-methylimidazole (1.45 ml, 18.3 mmol) in DCM (60 ml). The reaction mixture is stirred overnight at rt, then extracted/washed with saturated solution of NaHCO3 (2 x 100 ml), 3% aqueous citric acid (2 x 100 ml) and dried over Na2SO4. The organic phase is concentrated in vacuo and the product is obtained by flash chromatography on silica gel using linear gradient of ethanol in chloroform in 71% yield (1.42 g, 2.16 mmol) in the form of colorless wax. A mixture of diastereoisomers ~ 1:1 1H NMR (500.0 MHz, CDCl3): 0.88 (m, 6H, CH3(CH2)15); 1.23-1.33 (m, 52H, CH3(CH2)13CH2CH2-O); 1.348, 1.352 (2 * q, 2 * 3H, 4J= 0.6, (CH3)2C); 1.54 (m, 4H, CH3(CH2)13CH2CH2O); 1.57 (s, 6H, (CH3)2C); 1.92, 1.94 (2 * p, 2 * 2H, Jvic = 6.1, OCH2CH2CH2OC16H33); 3.38, 3.39 (2 * t, 2 * 2H, Jvic, = 6.7, CH3(CH2)13CH2CH2O); 3.48, 3.49 (2 * t, 2 * 2H, Jvic = 6.1, OCH2CH2CH2OC16H33); 4.13, 4.15 (2 * td, 2 * 2H, Jvic = 6.1, JH,P = 4.8, OCH2CH2CH2OC16H33); 4.20-4.30 (m, 4H, H-5′); 4.34-4.38 (m, 2H, H-4′); 4.85, 4.86 (2 * dd, 2 * 1H, J3′,2′ = 6.5, J3′,4′ = 3.6, H-3′); 4.92 (dd, 2H, J2′,3′ = 6.5, J2′,1′ = 2.3, H-2′); 5.700, 5.704 (2 * d, 2 * 1H, J5,6 = 8.1 H-5); 5.74, 5.76 (2 * d, 2 * 1H, J1′,2′ = 2.3, H-1′); 6.03, 6.05 (2 * ddd, 2 * 1H, JH,P = 22.9, Jtrans = 18.4, Jcis = 12.7, =CHP); 6.16, 6.18 (2 * ddd, 2 * 1H, JH,P = 51.8, Jcis = 12.7, Jgem = 1.9, CHcisHtrans=CHP); 6.33, 6.35 (2 * ddd, 2 * 1H, JH,P = 25.5, Jtrans = 18.4, Jgem = 1.9, CHcisHtrans=CHP); 7.34, 7.39 (2 * d, 2 * 1H, J6,5 = 8.1, H-6). 13C NMR (125.7 MHz, CDCl3): 14.07 (CH3(CH2)15); 22.62 (CH3(CH2)13CH2CH2O); 25.19, 25.21 ((CH3)2C); 26.08 (CH3(CH2)14CH2O); 27.04, 27.06 ((CH3)2C); 29.29, 29.45, 29.55, 29.57, 29.58, 29.63 (CH3(CH2)14CH2O); 30.66, 30.68 (d, JC,P = 6.4, OCH2CH2CH2OC16H33); 31.85 (CH3(CH2)13CH2CH2O); 63.56 63.57 (d, JC,P = 5.5, OCH2CH2CH2OC16H33); 64.92, 65.01 (d, JC,P = 5.5, CH2-5′); 66.32, 66.36 (OCH2CH2CH2OC16H33); 71.15, 71.16 (CH3(CH2)14CH2O); 80.60, 80.67 (CH-3′); 84.44, 84.53 (CH-2′); 85.38, 85.62 (d, JC,P = 7.1, CH-4′); 93.82, 94.12 (CH-1′); 102.57, 102.64 (CH-5); 114.42, 114.46 (C(CH3)2); 124.75, 124.80 (d, JC,P = 184.0, =CHP); 136.75, 136.77 (d, JC,P = 1.9, CH2=CHP); 141.43, 141.48 (CH-6); 150.16 (C-2); 163.29, 163.32 (C-4). 31P NMR (202.3 MHz, CDCl3): 18.64, 18.80. IR vmax(KBr) 2925 (vs), 2854 (s), 1709 9vs, sh), 1696 (vs), 1630 (w), 1459 (m), 1421 (m), 1400 (w, sh), 1381 (m), 1270 (m, sh), 1250 (m, sh), 1109 (s), 1078 (s), 1028 (s), 1012 (s), 972 (m, sh), 859 (m), 762 (w), 548 (w), 514 (w) cm-1. HR-ESI C33H58O9N2P (M+H)+ calcd 657.3874; found 657.3876

The synthetic route of 23377-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ustav Organicke Chemie A Biochemie Av Cr, V.v.i.; Mikrobiologicky Ustav AV CR V.V.I.; Ustav Molekularni Genetiky Av Cr, V.v.i.; Trios, spol. s r.o.; EP2527351; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2240-88-2, 3,3,3-Trifluoropropan-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, Computed Properties of C3H5F3O, blongs to alcohols-buliding-blocks compound. Computed Properties of C3H5F3O

1.00 g (5.75 mmol) 2-bromo-5-hydroxypyridine, 0.66 g (5.75 mmol) 3,3,3-trifluoro-l- propanol and 1.51 g (5.75 mmol) triphenylphosphine are added to 50 mL THF. Then 1.32 g (5.75 mmol) di-tert-butyl azodicarboxylate are added and the reaction mixture is stirred at 60 °C for 3 h. The solvent is removed in vacuo and the crude product is purified by column chromatography (silica gel, PE/EtOAc). C8H7BrF3NO (M= 270.1 g/mol) ESI-MS: 270/272 [M+H]+ Rt (HPLC):0.94 min (method C)

The synthetic route of 2240-88-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/114578; (2014); A1;,
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Related Products of 558-42-9, 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. 558-42-9, name is 1-Chloro-2-methyl-2-propanol. A new synthetic method of this compound is introduced below.

A solution of 1-chloro-2-methyl-2-propanol (2.23 g, 97percent, 0.02 mol), potassium phthalimide (3.780 g, 98percent, 0.02 mol) and sodium iodide (60 mg, 4 mmol) in anhydrous DMF (40 mL) was heated to reflux overnight. The solvent was evaporated under reduced pressure. The resulting product was triturated with a mixture of 3:2 ethyl acetate/hexanes and the ensuing white precipitate was removed by filtration. The yellow filtrate was concentrated under reduced pressure and purified by flash chromatography in a mixture of 2:3 ethyl acetate/hexanes. The impure product thus isolated was triturated with hot hexanes (125 mL) and filtered to remove an insoluble white impurity. After evaporation of the solvent under reduced pressure, the obtained white solid was recrystallized in hexanes. The product was yielded as colorless crystals that were collected by filtration and dried under high vacuum (1.63 g, 37percent yield). m.p.: 104-105° C.; TLC Rf 0.20 (2:3 ethyl acetate/hexanes); FTIR (KBr): 3524, 3456, 3097, 3031, 2973, 2930, 1773, 1698, 1611, 1466, 1427, 1389, 1319, 1190, 1076, 990, 965, 912, 890, 838, 766, 724, 712, 638 cm-1; 1H-NMR(500 MHz, CDCl3): delta 1.26 (s, 6H, 2 CH3), 2.74 (s, 1H, OH), 3.75 (s, 2H, CH2), 7.72 (dd, 2H, Jo=5.44 Hz, Jm=3.04 Hz, 2 Hc),, 7.85 (dd, 2H, Jo=5.42 Hz, Jm=3.06 Hz, 2 Hb); 13C-NMR(126 MHz, CDCl3): delta 27.6 (2 CH3), 49.3 (CH2), 71.6 (CMe2), 123.6 (2 Cb), 132.0 (2 Ca), 134.3 (2 Cc), 169.3 (2 CO).

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; DRAXIS Specialty Pharmaceuticals Inc.; US2008/102028; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 100058-61-5, 3-(Benzyloxy)cyclobutanol, 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, 100058-61-5, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

To a solution of 3-benzyloxycyclobutanol (5.0 g, 28.0 mmol) in dichloromethane (40 mL)was added dropwise diethylaminosulfur trifluoride (7.41 mL, 56.1 mmol) at 0 C. Thereaction was stirred at 15 C for 16 h and quenched with ice water (50 mL). Saturated aqueous sodium bicarbonate was added (100 mL), and the mixture was extracted with dichloromethane (200 mL). The organic phase was washed with brine (100 mL), dried over sodium sulfate and concentrated. The crude product was purified by flash column chromatography (eluting gradient: 10% ethyl acetate in petroleum ether) to give (3- fluorocyclobutoxy)methylbenzene (1.30 g, 26%) as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100058-61-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BRYAN, Marian C.; DO, Steven; DROBNICK, Joy; GOBBI, Alberto; KATSUMOTO, Tamiko; KIEFER, JR., James Richard; LIANG, Jun; RAJAPAKSA, Naomi S.; CHEN, Yongsheng; FU, Liqiang; LAI, Kwong Wah; LIU, Zhiguo; WAI, John; WANG, Fei; (322 pag.)WO2018/234345; (2018); A1;,
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Electric Literature of 13330-96-6 , The common heterocyclic compound, 13330-96-6, name is 4-(Dimethylamino)butan-1-ol, 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.

Example 36; 2-Butoxy-8-hydroxy-9-{3-[(4-dimethylaminobutoxy)carbonylmethyl]benzyl}adenine; 2-Butoxy-8-hydroxy-9-(3-carboxymethylbenzyl)adenine (88mg, 0.24mmol)which was prepared in Reference example 76 was suspended in DMF (10ml). Thereto were added at 0C 4-dimethylaminobutanol (0.16 ml, 1.18mmol), 1-hydroxybenzotriazole (0.16g, 1.18mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.23g, 1.18 mmol) in this order and the mixture was stirred at room temperature for 6 hours. After removal of the solvent by an evaporator, an aqueous saturated sodium bicarbonate solution was added to this residue and the resulted precipitate was filtered, followed by washing with water to give the titled compound as a white solid (73mg, 0.16mmol). Yield: 65% 1H NMR(DMSO-d6)delta 9.97(1H, brs), 7.20(4H, m), 6.45(2H, brs), 4.82(2H, s), 4.14(2H, t, J = 6.6 Hz), 4.00(2H, t, J = 6.6 Hz), 3.62(2H, s), 2.11(2H, t, J = 7.0 Hz), 2.04(6H, s), 1.62(2H, m), 1.51 (2H, m), 1.36(4H, m), 0.90(3H, t, J = 7.4 Hz).

The synthetic route of 13330-96-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; AstraZeneca AB; EP1728792; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4704-94-3, 2-(Hydroxymethyl)propane-1,3-diol, 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, blongs to alcohols-buliding-blocks compound. Safety of 2-(Hydroxymethyl)propane-1,3-diol

To a solution of 2-(hydroxymethyl)propane-l,3-diol (1 g) in THF (20 mL) were added 2,2-dimethoxypropane (1.344 mL) and para-toluenesulfonic acid monohydrate (0.054 g). The reaction mixture was stirred at room temperature for 4 hours, treated with TEA and concentrated. The concentrate was purified by flash chromatography (Analogix SF25chi40g with 20-30percent ethyl acetate/hexanes). MS (ESI) m/z 147.0 (M+l)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4704-94-3, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; WO2009/129385; (2009); A1;,
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Application of 575-03-1, 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 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a magnetically-stirred solution of 7-hydroxycoumarin derivatives (2 mmol), aromatic aldehydes (2 mmol) and NEt3 (2 mmol) in THF (8 mL) a mixture of dialkyl acetylenedicarboxylate (2 mmol) in THF (2 mL) was added in 15 min. The reaction mixture was then allowed to stand at room temperature for 0.5-10 h. After completion of the reaction as indicated by thin-layer chromatography (TLC) (n-hexane/EtOAc, 1:1), the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (Merck, 230-400 mesh) using a mixture of n-hexane/EtOAc (1:1) as eluent to afford the pure product as a light yellow powder.

According to the analysis of related databases, 575-03-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Asghari, Sakineh; Baharfar, Robabeh; Darabi, Samaneh Ahangar; Mohammadian, Reza; Journal of the Brazilian Chemical Society; vol. 26; 2; (2015); p. 218 – 223;,
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Application of 14320-38-8, 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.14320-38-8, name is Cyclopent-3-enol, molecular formula is C5H8O, molecular weight is 84.12, as common compound, the synthetic route is as follows.

To an ice-cooled solution of 4-hydroxycyclopentene (50.0 g, 0.594 mol) and imidazole (80.9 g, 1.19 mol) in N,N-dimethylformamide (300 mL) was slowly added tert-butyldiphenylsilyl chloride (180 g, 0.65 mmol). The reaction mixture was warmed to room temperature. After 16 h, the reaction mixture was diluted with water (1 L) and ethyl acetate (500 mL). The aqueous layer was extracted with ethyl acetate (2*200 mL). The combined organics were washed sequentially with water (3*300 mL) and saturated aqueous sodium chloride solution (2*200 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (15:1 petroleum ether/ethyl acetate) provided tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane (188 g, 98%) as a colorless oil. 1H NMR (400 MHz, CDCl3): delta 7.69-7.66 (m, 4H), 7.43-7.38 (m, 6H), 5.63-5.60 (m, 2H), 4.58-4.53 (m, 1H), 2.46-2.38 (m, 4H), 1.61 (s, 9H).

The chemical industry reduces the impact on the environment during synthesis 14320-38-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; Siu, Michael; Estrada, Anthony; Liu, Wen; Lyssikatos, Joseph P.; Patel, Snahel; Liang, Guibai; Chen, Kevin; US2015/175619; (2015); A1;,
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