Month: September 2021

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.80379-31-3, name is Ethyl 3-hydroxy-2H-chromene-4-carboxylate, molecular formula is C12H12O4, molecular weight is 220.22, as common compound, the synthetic route is as follows.Safety of Ethyl 3-hydroxy-2H-chromene-4-carboxylate

The sodium metal (10 mg, 0.4 mmol) was added to absolute EtOH (400 muL) at room temperature and stirred for 30 min until the solid was dissolved. Guanidine hydrochloride (28.5 mg, 0.3 mmol) and 2a (44 mg, 0.2 mmol) were added to the solution and raise the temperature to 80 C with stirring overnight. Saturated aqueous NH4Cl solution (1 mL) was added to neutralize the reaction. The resulting mixture was extracted with EtOAc (10 mL×2), washed with brine, dried over Na2SO4, and concentrated. The residue was purified on silica gel (CH2Cl2/MeOH, 30:1) to get the product as a colorless solid (37 mg, 86%). 1H NMR (400 MHz, DMSO-d6): delta 11.80 (s, 1H), 8.38 (dd, J=1.6, 7.6 Hz, 1H), 7.05-7.02 (m, 1H), 6.94-6.90 (m, 1H), 6.84-6.82 (m, 2H), 4.75 (s, 2H), 3.17 (d, J=5.6 Hz, 1H); 13C NMR (100 MHz, DMSO-d6): delta 159.47, 158.96, 155.29, 151.39, 126.31, 124.72, 121.48, 120.70, 115.55, 101.70, 67.92 ppm; HRMS (ESI): m/z [M+H]+ calcd for C11H10N3O2 216.0773, found 216.0767.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,80379-31-3, Ethyl 3-hydroxy-2H-chromene-4-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Xiaolin; Lei, Mei; Zhang, Yi-Nan; Hu, Li-Hong; Tetrahedron; vol. 70; 21; (2014); p. 3400 – 3406;,
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Application of 927-74-2, Adding some certain compound to certain chemical reactions, such as: 927-74-2, name is 3-Butyn-1-ol,molecular formula is C4H6O, 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 927-74-2.

General procedure: To a solution of 3-butyn-1-ol 10 (1.2 equiv.) in tert-BuOH (40 mL) and H2O (40 mL), CuSO4·5H2O (0.25 equiv.), sodium ascorbate (0.5 equiv.), aryl/alkyl azide 9 (1.1 equiv.) and triethylamine (1.0 equiv.) were added. The mixture was stirred at r.t. under N2 for 4 h, and then concentrated in vacuo. The residue was extracted with CH2Cl2 (3 × 30 mL). The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained triazoles were used for the next reaction without further purification.

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. 927-74-2, 3-Butyn-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Giofre, Salvatore V.; Romeo, Roberto; Carnovale, Caterina; Mancuso, Raffaella; Cirmi, Santa; Navarra, Michele; Garozzo, Adriana; Chiacchio, Maria A.; Molecules; vol. 20; 4; (2015); p. 5260 – 5275;,
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Synthetic Route of 4654-39-1 ,Some common heterocyclic compound, 4654-39-1, molecular formula is C8H9BrO, 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.

Dissolve 31.6 g of iodine, 33.9 g of triphenylphosphine and 22.4 mg of imidazole in anhydrous dichloromethane (100 mL), After cooling in an ice bath for 30 minutes, 20.0 g of p-bromobenzyl alcohol was dissolved in anhydrous dichloromethane (50 mL) and quickly added dropwise to the reaction bottle.Remove the ice bath and react at room temperature for about 6 hours.Distill off the methylene chloride, add a water-methanol mixture solution (400mL, water: methanol volume ratio of 1:3), transfer to a separatory funnel, add n-heptane extraction (200mL×3), shake vigorously until the whole system is free The color is transparent and the organic layers are combined.It was dried over anhydrous sodium sulfate, and the organic solvent was distilled off to obtain a colorless transparent solid, that is, compound 11. The product was stored in the dark and the yield was 93.2%.

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. 4654-39-1, 2-(4-Bromophenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Shi Zeyu; Chen Si; Xiao Qiong; Zhang Xiang; Tian Yulin; Yin Dali; (11 pag.)CN111087358; (2020); A;,
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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.60211-57-6, name is 3,5-Dichlorobenzyl alcohol, molecular formula is C7H6Cl2O, molecular weight is 177.0279, as common compound, the synthetic route is as follows.Application In Synthesis of 3,5-Dichlorobenzyl alcohol

Step 1.Preparation of {7-[4-(3,5-Dichloro-benzyloxy)-benzylsulfanyl]-indan-4-yloxy}-acetic Acid Methyl Ester (Compound 77A) The product from Example 75C (0.42 g, 1 mmoles), (3,5-dichlorophenyl)-methanol (0.24 g, 1.3 mmoles), triphenyl phosphine (0.38 g, 1.5 mmoles), and 0.23 ML of diethyl azodicarboxylate (0.25 g, 1.5 mmoles) were dissolved in 9 ML of tetrahydrofuran.The reaction mixture was stirred at room temperature under nitrogen for 18 hrs.The reaction mixture was evaporated to give a residue, which was flash chromatographed (silica gel, 20% ethyl acetate in hexane) to afford the title compound in good purity. MS m/z 265

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60211-57-6, 3,5-Dichlorobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Patent; Auerbach, Bruce J.; Bratton, Larry D.; Filzen, Gary F.; Geyer, Andrew G.; Trivedi, Bharat K.; Unangst, Paul C.; US2003/225158; (2003); A1;,
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Synthetic Route of 61439-59-6, Adding some certain compound to certain chemical reactions, such as: 61439-59-6, name is 2-(4-(Benzyloxy)phenyl)ethanol,molecular formula is C15H16O2, 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 61439-59-6.

(a) A solution of 3.51 g of methanesulfonyl chloride in 5 ml of diethyl ether was added dropwise over a period of 0.5 hour to a stirred solution of 7.0 g of 4-benzyloxyphenethyl alcohol in 20 ml of pyridine at 0° C. Stirring was continued for 2 hours while the mixture was allowed to warm to room temperature: The mixture was then partitioned between 150 ml of 2 N hydrochloric acid and dichloromethane. The organic phase was separated, washed with water, dried over sodium sulfate, filtered, and evaporated. Trituration of the residue with n-hexane brought about crystallization. The crystals were removed by filtration and dried, whereby 8.9 g (95percent) of 1-benzyloxy-4-(2-methanesulfonyloxyethyl)benzene having a melting point of 60°-64° C. were obtained.

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. 61439-59-6, 2-(4-(Benzyloxy)phenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US4387100; (1983); A;,
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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. Computed Properties of C9H12O

General procedure: Firstly, GO (0.01 g) was added into water (3 mL) and the mixturecould generate the stable colloidal suspensions under a mild ultrasonictreatment. Afterwards, the alcohol (2 mmol) and (NH4)5H5[H2(WO4)6](0.03 mmol, M=1602) were added. The mixture was stirred for 15 min atroom temperature. Subsequently, hydrogen peroxide (30 wt%, 8 mmol)was added dropwise and the mixture was heated to 70C until thereaction was fully completed (monitored by TLC). After the reactioncompleted, GO could be readily separated from the mixtures bycentrifugation, and then ethyl acetate was added to the mixture to extract organic constituents. Finally, the organic extracts were concentratedunder reduced pressure and purified by column chromatography.

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

Reference:
Article; Fu, Huihui; Hu, Chuanfeng; Huang, Zhida; Zhou, Jianhao; Peng, Xinhua; Synlett; vol. 29; 4; (2018); p. 447 – 451;,
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Adding a certain compound to certain chemical reactions, such as: 3344-77-2, 12-Bromododecan-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: C12H25BrO, blongs to alcohols-buliding-blocks compound. COA of Formula: C12H25BrO

vi) Cholesteryl 12-hydroxydodecylcarbamate from cholesteryl chloroformate and 12-aminododecan-1-ol. 12-Aminododecanl-1-ol is prepared from 12-bromododecan-1-ol and sodium azide in refluxing 95% ethanol, followed by catalytic hydrogenation (10% Pd/C catalyst, 30 psi hydrogen) in methanol.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3344-77-2, 12-Bromododecan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Dharmacon, Inc.; US2008/85869; (2008); A1;,
Alcohol – Wikipedia,
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Related Products of 1875-88-3 ,Some common heterocyclic compound, 1875-88-3, molecular formula is C8H9ClO, 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.

(9A) Ethyl 3-{4-[2-(4-chlorophenyl)ethoxy]phenyl}-3-ethoxypropionate Ethyl 3-ethoxy-3-(4-hydroxyphenyl)propionate (100 mg, 0.420 mmol) produced in Example 1 (1C) and 2-(4-chlorophenyl)ethanol (99 mg, 0.630 mmol) were dissolved in tetrahydrofuran (10 mL), and triphenylphosphine (178 mg, 0.680 mmol) and a 40percent diethyl azodicarboxylate toluene solution (309 muL, 0.680 mmol) were added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 50° C. for 4 hours. After the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound was obtained as a yellow oily substance (151 mg, yield: 95percent). 1H NMR (CDCl3, 400 MHz): delta1.13 (3H, t, J=7.0 Hz), 1.23 (3H, t, J=7.0 Hz), 2.55 (1H, dd, J=5.0, 15.2 Hz), 2.79 (1H, dd, J=9.0, 15.2 Hz), 3.06 (2H, t, J=7.0 Hz), 3.30-3.38 (2H, m), 4.14 (4H, t, J=7.3 Hz), 4.68 (1H, dd, J=5.0, 8.9 Hz), 6.86 (2H, d, J=8.6 Hz), 7.22 (2H, d, J=8.3 Hz), 7.24 (2H, d, J=8.6 Hz), 7.28 (2H, d, J=8.6 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1875-88-3, its application will become more common.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; US2011/53974; (2011); A1;,
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Reference of 627-30-5 ,Some common heterocyclic compound, 627-30-5, molecular formula is C3H7ClO, 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 4-CHLORO-7- (3-CHLOROPROPOXY)-6-METHOXYQUINAZOLINE used as a starting material was prepared as follows:- Ammonium formate (45 g) was added portionwise over 1.25 hours to a stirred mixture of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (International Patent Application WO 02/16352, Example 1 thereof; 20 g), 10% palladium-on-carbon catalyst (3.3 g) and DMF (530 ml) and the reaction mixture was stirred for an additional 30 minutes. The catalyst was removed by filtration and the solvent was evaporated. There was thus obtained 7-hydroxy- 6-methoxy-3,4-dihydroquinazolin-4-one (8.65 g); NMR Spectrum: (DMSOD6) 3.9 (s, 3H), 7.0 (s, 1H), 7.45 (s, 1H), 7.9 (s, 1H). A mixture of the material so obtained, acetic anhydride (63 ml) and pyridine (7.5 ml) was heated to 100C for 4.5 hours. The resultant mixture was allowed to stand at ambient temperature for 16 hours. The mixture was poured into a stirred mixture (400 ml) of ice and water. The resultant precipitate was isolated and dried under vacuum. Analysis revealed that hydrolysis of the acetate group on the 4 position of the quinazoline was incomplete. The mixture was therefore further hydrolysed with water (150 ml) and pyridine (a few drops) at 90C for 15 minutes. The resultant mixture was cooled to ambient temperature and the solid was collected by filtration, washed with water and dried under vacuum. There was thus obtained 7-ACETOXY-6-METHOXY-3, 4-dihydroquinazolin-4-one (7.4 g); NMR Spectrum: (DMSOD6) 2.3 (s, 3H), 3.9 (s, 3H), 7.45 (s, 1IN), 7.65 (s, 1H), 8. 05 (s, 1H). A mixture of A portion (2 g) of the material so obtained, thionyl chloride (32 ml) and DMF (5 drops) was stirred and heated to reflux for 1.5 hours. The mixture was cooled to ambient temperature and the excess of thionyl chloride was evaporated. Toluene was added to the residue and evaporated. The resultant residue was diluted with methylene chloride (15 ml) and a 10% ammonia solution in methanol (80 ml) was added and the mixture was heated to 80C for 10 minutes. The mixture was cooled to ambient temperature and evaporated. Water was added to the residue and the mixture was neutralised by the addition of dilute aqueous hydrochloric acid solution. The resultant precipitate was collected by filtration and dried under vacuum at 35C for 16 hours. There was thus obtained 4-chloro- 7-hydroxy-6-methoxyquinazoline (1.65 g); NMR Spectrum: (DMSOD6) 4.0 (s, 3H), 7.25 (s, 1H), 7.4 (s, 1H), 8.8 (s, 1H). Di-tert-butyl azodicarboxylate (2.3 g) was added portionwise over a few minutes to a stirred mixture of 4-chloro-7-hydroxy-6-methoxyquinazoline (1.65 g), 3-chloropropanol (0.7 ml), triphenylphosphine (2.6 g) and methylene chloride (100 ml) and the reaction mixture was stirred at ambient temperature for 2 hours. The mixture was concentrated to a volume of about 30 ml by evaporation and the residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether (b. p 40-60C) and ethyl acetate as eluent. There was thus obtained 4-CHLORO-7- (3-CHLOROPROPOXY)-6-METHOXYQUINAZOLINE as a white solid (2 g); NMR Spectrum: (DMSOD6) 2.3 (m, 2H), 3. 8 (m, 2H), 4.05 (s, 3H), 4.4 (m, 2H), 7.45 (s, 1H), 7.55 (s, 1H), 8.9 (s, 1H).

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. 627-30-5, 3-Chloropropan-1-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/81000; (2004); A1;,
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Related Products of 5182-44-5 ,Some common heterocyclic compound, 5182-44-5, molecular formula is C8H9ClO, 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.

2-(3-chlorophenyl)acetaldehyde[115] The mixture of Example 86A (5.73 g, 36.5 mmol) and Dess-Martin periodinane (18.6 g, 43.8 mmol) in 200 mL of dichloromethane was stirred under 2 atmosphere for 4 hours at room temperature. Then saturated aHC03 (500 mL) and a2S2C>3 (100 mL) was added with stirring for another 30 minutes. The mixture was extracted with dichloromethane (3 x 300 mL). The organic layers were combined, dried over Na2S04, filtered, and concentrated. The crude product was purified by distillation under reduced pressure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5182-44-5, its application will become more common.

Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62966; (2013); A2;,
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