Author: tianli

Reference of 33420-52-9, 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. 33420-52-9, name is 2,2-Difluoropropan-1-ol. A new synthetic method of this compound is introduced below.

G. (R)-3-[N-(5′-Chloro-2′-fluoro-iphenyl-4-ylmethyl)-N’-oxalylhydrazino]-2-hydroxypropionic Acid 2,2-Difluoropropyl Ester (R)-3-[N’-t-Butoxyoxalyl-N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)hydrazino]2-hydroxy-propionic acid (15.0 mg, 32 mumol) was combined with HOBt (26.0 mg, 193 mumol) and EDC (34 muL, 0.2 mmol) in DCM (0.2 mL, 4 mmol). The solution was stirred for 10 minutes and 2,2-difluoropropanol (24.7 mg, 257 mumol) was added. The reaction was stirred at room temperature and monitored for completion. After 2 hours, the mixture was concentrated by rotary evaporation and the solvent was removed in vacuo. The resulting residue was dissolved in DCM (124 muL, 1.9 mmol). TFA (124 muL, 1.6 mmol) was added, and the resulting mixture was stirred for 2 hours. The solvent was removed in vacuo and the residue was purified by preparative HPLC to yield the title compound (2.2 mg). MS m/z [M+H]+ calc’d for C21H2O ClF3N2O6, 489.10; found 489.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,33420-52-9, 2,2-Difluoropropan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; HUGHES, Adam D.; FENSTER, Erik; FLEURY, Melissa; GENDRON, Roland; US2013/109639; (2013); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 2568-33-4, Adding some certain compound to certain chemical reactions, such as: 2568-33-4, name is 3-Methylbutane-1,3-diol,molecular formula is C5H12O2, 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 2568-33-4.

A 50 mL three-necked flask that had been equipped with a column fitted with a side tube and packed with 20 g of molecular sieve (4A), a condenser, a thermometer and a drying tube was loaded with 0.64 g (2 mmol) of N, N?-bis(salicylidene)ethylenediamine iron (II), 1.04 g (10 mmol) of isoprene glycol, 40 g (400 mmol) of methyl methacrylate, 0.08 g of phenothiazine and 0.2 g of tridecane. While performing stirring at atmospheric pressure, the flask was placed into an oil bath set at 120 C. so that the temperature inside the flask would be 100 to 105 C. The reaction was performed for 11 hours while totally refluxing the distilled fraction back to the reaction system through the molecular sieve. The reaction liquid was sampled at prescribed lapses of time from the start of the reaction (3 hours, 5 hours, 7 hours, 9 hours and 11 hours). The gelation of the samples of the reaction liquid was evaluated as described in Test Example 3, the results being described in Table 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. 2568-33-4, 3-Methylbutane-1,3-diol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KURARAY CO., LTD.; TAKAHATA, Yusuke; KAJIYASHIKI, Tsuyoshi; (9 pag.)US2018/50975; (2018); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 3068-00-6, 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.3068-00-6, name is 1,2,4-Butanetriol, molecular formula is C4H10O3, molecular weight is 106.1204, as common compound, the synthetic route is as follows.

General procedure: Xantphos (28.9 mg, 0.05 mmol), Cs2CO3 (32.6 mg, 0.10 mmol) and [Ru(p-cymene)Cl2]2 (15.3 mg, 0.025 mmol) were added to a Schlenk tube. Then the tube was evacuated and refilled with nitrogen. Dry toluene as solvent (2.0 mL)were added and the solution was stirred at room temperature under nitrogen for 30 min. Activated molecular sieves 4A (0.10 g) and triol 6a (106.1 mg, 1.00 mmol) were then added. And the solution was stirred at room temperature under nitrogen for 40 min. Subsequently, aniline 5a (46.6 mg, 0.50 mmol) was added and the solution was stirred at room temperature under nitrogen for 20 min. Then the resulting solution was heated to reflux and stirred for 48 h. The reaction was monitored by TLC. After completion, the solution was filtered through a plug of Celite and washed with EtOAc (3 mL x 3). The filtrate was concentrated under vacuum. Purification via flash column chromatography with silica gel (eluting with PE/EA = 5/1 (v/v)) yielded 4a (43.0 mg, 81% yield) as light yellow oil.

Statistics shows that 3068-00-6 is playing an increasingly important role. we look forward to future research findings about 1,2,4-Butanetriol.

Reference:
Article; Xu, Qing-Song; Li, Chen; Xu, Yong; Xu, Defeng; Shen, Mei-Hua; Xu, Hua-Dong; Chinese Chemical Letters; (2019);,
Alcohol – Wikipedia,
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Electric Literature of 2854-16-2 ,Some common heterocyclic compound, 2854-16-2, molecular formula is C4H11NO, 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 444-(cyclopropylmethoxy)-N-(2-{[(2-hydroxy-2-methylpropyl)amino]methyl}-4-methyl-1H-indol-5-yl)benzamide4-(Cyclopropylmethoxy)-N-(2-formyl-4-methyl-1H-indol-5-yl)benzamide (298 mg) obtained in Reference Example 41 and 1-amino-2-methylpropan-2-ol (153 mg) were suspended in NMP (3.0 mL), acetic acid (1.0 mL) was added at room temperature, and the mixture was stirred at the same temperature for 2 hr.Sodium triacetoxyborohydride (363 mg) was added, the mixture was stirred at room temperature for 16 hr, and diluted with ethyl acetate, and 2N aqueous sodium hydroxide solution (20 mL) was added at room temperature.The mixture was poured into water, and the organic layer was washed with water and then with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure.The residue was suspended in ethyl acetate, and the precipitate was collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give the title compound (307 mg, yield 85percent) as a brown solid.1H NMR (300 MHz, CDCl3) delta: 0. 34 – 0.43 (2 H, m), 0.63-0.72 (2 H, m), 1.22 (6 H, s), 1.25 – 1.36 (1 H, m), 2.45 (3 H, s), 2.61 (2 H, s), 3.88 (2 H, d, J=7.2 Hz), 4.02 (2 H, s), 6.38 (1 H, d, J=1.1 Hz), 6.98 (2 H, d, J=8.3 Hz), 7.19 (1 H, d, J=8.3 Hz), 7.34 (1 H, d, J=7.6 Hz), 7.58 (1 H, br. s.), 7.88 (2 H, d, J=8.0 Hz), 8.48 (1 H, br. s.).melting point: 186¡ãCelemental analysis (C25H31N3O3*0.2H2O)Calculated: C, 70.63; H, 7.44; N, 9.88.Found: C, 70.57; H, 7.38; N, 9.68.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,2854-16-2, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2522657; (2012); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 202865-66-5, 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. 202865-66-5, name is (2-Bromo-5-fluorophenyl)methanol, molecular formula is C7H6BrFO, 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.

1)Synthesis of 5-bromo-2-fluoro-4-(hydroxymethyl)benzaldehydeTetramethylpiperidine (0.68 g, 4.87 mmol) was dissolved in tetrahydrofuran (4.5 mL).To the resultant solution was added n-butyllithium (1.0 M n-hexane solution, 4.88 mL) at 0¡ã C., and this solution was stirred for 15 minutes.The resultant mixture was cooled to -78¡ã C. and a solution of (2-bromo-5-fluorophenyl)methanol (0.50 g, 2.43 mmol) in tetrahydrofuran (2.5 mL) was added dropwise thereto.The temperature of the solution was raised over 2 hours to -40¡ã C.The solution was again cooled to -78¡ã C., and then dimethylformamide (0.47 mL, 6.07 mmol) was added thereto.The temperature of the solution was raised to room temperature, and the solution was stirred for 30 minutes.Saturated aqueous ammonium chloride was then added thereto, and the resultant mixture was extracted with ethyl acetate.The organic layer was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, to thereby obtain the titled compound (604.3 mg, quantitative).1H-NMR (CDCl3) delta: 4.78 (2H, s), 7.46 (1H, d, J=10.6 Hz), 8.01 (1H, d, J=6.2 Hz), 10.29 (1H, s).

According to the analysis of related databases, 202865-66-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; US2011/275703; (2011); A1;,
Alcohol – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 558-42-9, 1-Chloro-2-methyl-2-propanol, 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, Product Details of 558-42-9, blongs to alcohols-buliding-blocks compound. Product Details of 558-42-9

To a suspension of I-47 (336 mg, 0.93 mmol) and potassium carbonate (154 mg, 1.12 mmol) in DMF (6 mL) is added 1-chloro-2-methyl-propan-2-ol (100 muL, 0.98 mmol). The reaction mixture is stirred at 80¡ã C. for 16 h then concentrated in vacuo. The residue is extracted with CH2Cl2, washed with saturated aqueous NH4Cl, dried with Na2SO4, filtered and concentrated in vacuo to afford I-104 (365 mg); m/z 434 [M+H].

The synthetic route of 558-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; BYLOCK, Lars Anders; US2013/195879; (2013); A1;,
Alcohol – Wikipedia,
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Reference of 3279-95-6, 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 3279-95-6 as follows.

Preparation of (4R)-4-((3R, 5S, 6R, 7R, 10S, 13R)-6-ethyl-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenant hrene-17-yl)-N-(2-hydroxyethoxy)pentanamide 6alpha-Ethyl-chenodeoxycholic acid (OCA, 30 mg, 0.07 mmol) and compound 8-ii (6.5 mg, 0.085 mmoL) were dissolved in dichloromethane, and added with TBTU (40 mg, 0.11 mmoL) and DIPEA (30 muL, 0.21 mmoL) successively. The reaction solution was stirred at room temperature overnight. After TLC showed the disappearance of starting material, water was added, and the reaction solution was extracted with ethyl acetate. The organic phase was concentrated under reduced pressure and the residures were purified by column chromatography to obtain compound 8(10 mg, 30%). 1H NMR (400 MHz, MeOD) delta 3.95 – 3.85 (m, 1H), 3.74 (dt, J= 16.4, 4.7 Hz, 2H), 3.67 (s, 1H), 3.35 – 3.32 (m, 1H), 1.00 (d, J= 6.5 Hz, 3H), 0.95 – 0.89 (m, 6H), 0.72 (s, 3H). 13C NMR (101 MHz, MeOD) delta 172.75, 77.45, 71.80, 69.78, 59.02, 55.86, 50.29, 48.46, 45.57, 42.37, 41.77, 40.17, 39.65, 35.40, 35.25, 33.15, 33.04, 31.49, 29.87, 29.32, 27.90, 23.17, 22.36, 22.10, 20.59, 17.47, 10.85, 10.64.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3279-95-6, its application will become more common.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Shanghai Hansoh Biomedical Co., Ltd.; LU, Aifeng; ZHONG, Huijuan; LI, Chenghai; BAO, Rudi; LV, Aifeng; (40 pag.)EP3290429; (2018); A1;,
Alcohol – Wikipedia,
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Reference of 13826-35-2 ,Some common heterocyclic compound, 13826-35-2, molecular formula is C13H12O2, 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.

a. 3-Phenoxybenzaldehyde Chromium trioxide (3.00 g.) was added to a stirred solution of pyridine (4.75 g.) in dry methalene chloride (75 ml.), and stirring was continued for a further 15 minutes. 3-Phenoxybenzyl alcohol (1 g.) in methylene chloride (5 ml.) was added, the mixture stirred for a further 15 minutes, decanted and the residue washed with diethyl ether (100 ml.). The filtrate was washed with 55 sodium hydroxide solution (3 * 50 ml), 2.5 NHCl (50 ml.) and 5% sodium carbonate solution (50 ml.) and dried over Na2 SO4 to give 3-phenoxy-benzaldehyde. Alternatively the alcohol can be oxidized using Jones’ reagent, a similar yield of aldehyde being 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. 13826-35-2, (3-Phenoxyphenyl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; National Research Development Corporation; US4024163; (1977); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 25574-11-2, 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.25574-11-2, name is 3-(4-Bromophenyl)propan-1-ol, molecular formula is C9H11BrO, molecular weight is 215.087, as common compound, the synthetic route is as follows.

Under a nitrogen atmosphere, DPPA (diphenylphosphoryl azide) (2 eq) and l,8-Diazabicycloundec-7-ene (DBU) (2 eq) were subsequently added to a cooled (0 C) solution of the corresponding alcohol (4) (1 eq) in dry Nu,Nu’- dimethylformamide (0.4 M). After 0.5 h. NaN3 (2 eq) was added and the reaction mixture was heated for 3 h. at 100 C. After cooling to room temperature, the reaction was worked up by dilution with water and extraction with diethyl ether (x5). The combined organic layers were washed with water (x2), brine (xl), dried over sodium sulfate and concentrated in vacuo. Finally the crude material was purified by column chromatography to give the desired azide 3-(l-(8-azidooctyl)-lH-l,2,3-triazol-4-yl)pyridine ; The title compound was prepared from (54) according to the general procedure of example 5, but the reaction mixture was heated to 50 C for 24 h. The crude material was purified by column chromatography using PE/EtOAc 98:2 as eluant, to give a colorless oil; yield 79%; IR (KBr) 2941, 2097, 1488, 1254, 1072, 1011, 831, 795 cm”1; 1H- MR (300 MHz, CDC13) delta 7.41 (dd, J = 6.4/1.8 Hz, 2-H), 7.06 (dd, J = 6.4/1.8 Hz, 2-H), 3.28 (t, J= 6.7 Hz, 2-H), 2.66 (t, J = 7.3 Hz, 2-H), 1.88(quint, J = 6.7 Hz, 2-H) ppm; 1 C-NMR (75 MHz, CDC13) delta 139.9, 131.7, 130.3, 120.0, 50.6, 32.2, 30.4 ppm.

The chemical industry reduces the impact on the environment during synthesis 25574-11-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; UNIVERSITA DEGLI STUDI DEL PIEMONTE ORIENTALE “AMEDEO AVOGADRO”; GENAZZANI, Armando A.; TRON, Gian Cesare; GALLI, Ubaldina; TRAVELLI, Cristina; CUZZOCREA, Salvatore; GROSA, Giorgio; SORBA, Giovanni; CANONICO, Pier Luigi; WO2014/178001; (2014); A1;,
Alcohol – Wikipedia,
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Electric Literature of 2077-19-2, 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.2077-19-2, name is 2-(4-Bromophenyl)propan-2-ol, molecular formula is C9H11BrO, molecular weight is 215.09, as common compound, the synthetic route is as follows.

A flask was charged with 2-(4-bromophenyl)propan-2-ol (5.00 g, 23.3 mmol, Bioorg. Med. Chem. Lett. 2007, 17, 662), 4,4,4 45,5,55′-octamethyl-2,2′-bi(l,3,2- dioxaborolane) (6.49 g, 25.6 mmol), KOAc (6.84 g, 69.7 mmol), PdCl2(dppf) (0.949 g, 1.16 mmol) and DMSO (155 mL). The mixture was heated to about 80 C for about 4 h. After cooling to rt, the mixture was partitioned between brine (400 mL) and EtOAc (100 mL). The organic layer was isolated and the aqueous phase was extracted with two further portions of EtOAc (2 x 50 mL). The organic layers were combined, washed with brine (5 x 100 mL), dried over anhydrous MgS04 and concentrated in vacuo. The crude material was purified by silica gel flash chromatography with a gradient of 0 to 100% EtOAc/hexanes to give 2-(4-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)propan-2-ol (2.76 g, 45%): 1H NMR (d-DMSO) delta 7.80 (s, J = 8, 2H), 7.50 (s, J = 8, 2H), 1.58 (s, 6H), 1.34 (s, 12H).

Statistics shows that 2077-19-2 is playing an increasingly important role. we look forward to future research findings about 2-(4-Bromophenyl)propan-2-ol.

Reference:
Patent; ABBVIE INC.; LI, Bin; BREINLINGER, Eric; DAVIS, Heather; HOEMANN, Michael; LI, Biqin; SOMAL, Gagandeep; VAN EPPS, Stacy; WANG, Lu; WO2014/169473; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts