Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane, 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, category: alcohols-buliding-blocks, blongs to alcohols-buliding-blocks compound. category: alcohols-buliding-blocks

Step 1: [1-({[tert-Butyl(dimethyl)silyl]oxy}methyl)cyclopropyl]methanol 1,1-Bis(hydroxymethyl)cyclopropane (1.0 g, 0.0098 mol), triethylamine (TEA) (2.0 mL, 0.015 mol), and 1H-imidazole (0.13 g, 0.0020 mol) were dissolved in anhydrous DCM (15 mL) and the solution was cooled to 0 C. A solution of tert-butyldimethylsilyl chloride (1.55 g, 0.0103 mol) in DCM (5 mL) was added drop-wise and the resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 and extracted with DCM (3*). The organic extract was dried (magnesium sulfate), filtered, and concentrated in vacuo. The crude product was identified by 1H NMR and used in the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane, and friends who are interested can also refer to it.

Reference:
Patent; Yao, Wenqing; Burns, David M.; Chen, Lihua; Zhuo, Jincong; He, Chunhong; US2007/197506; (2007); A1;,
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Synthetic Route of 1805-32-9, 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. 1805-32-9, name is 3,4-Dichlorobenzyl alcohol. A new synthetic method of this compound is introduced below.

General procedure: Ionic liquid [Dsim]HSO4 (6.5 mg, ?0.02 mmol) was added to a stirred mixture of alcohol, phenol or naphthol (1.0 mmol) and HMDS (80 mg, 0.5 mmol) at room temperature under solvent free conditions. After completion of the reaction (monitored by TLC, It should be noted that when addition of HMDS is finished stirring of the mixture is stopped after 1 min. TLC showed that in most of the cases the reaction is completed immediately after the addition of HMDS), the product was extracted with Et2O and the ionic liquid was recovered and was dried at 65 ?C under vacuum to remove moisture, and then reused. Evaporation of the solvent under reduced pressure gave the highly pure product without further purification. The desired pure products were characterized by comparison of their IR, NMR and MS data as well as boiling poin twith those of known compounds

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1805-32-9, 3,4-Dichlorobenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Article; Shirini, Farhad; Khaligh, Nader Ghaffari; Akbari-Dadamahaleh, Somayeh; Journal of Molecular Catalysis A: Chemical; vol. 365; (2012); p. 15 – 23;,
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Application of 702-23-8, 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.702-23-8, name is 2-(4-Methoxyphenyl)ethanol, molecular formula is C9H12O2, molecular weight is 152.19, as common compound, the synthetic route is as follows.

To a solution of 4-methoxyphenethyl alcohol (1.03 g, 6.77 mmol) in dichloromethane (20 mL) were added N,N-diisopropylethylamine (2.3 mL, 14 mmol) and chloromethyl methyl ether (0.82 mL, 11 mmol) at 0 C. The reaction mixture was stirred for 27 h at ambient temperature. The reaction mixture was then concentrated under reduced pressure. Column chromatography (silica gel, 34 g; n-hexane/ethyl acetate, 8:1) gave the title compound (1.19 g, 6.07 mmol, 89.6%) as a pale yellow oil. 1 H NMR (400 MHz, CDCl 3 ): delta 2.85 (t, J = 7.0 Hz, 2H), 3.30 (s, 3H), 3.72 (t, J = 7.0 Hz, 2H), 3.78 (s, 3H), 4.61 (s, 2H), 6.80-6.87 (m, 2H), 7.12-7.19 (m, 2H). 13 C NMR (100 MHz, CDCl 3 ): delta 35.5, 55.3, 55.4, 68.8, 96.5, 113.9, 129.9, 131.1, 158.2. HR-MS (EI): Calcd for C 11 H 16 O 3 [M] + : 196.1099. Found: 196.1093. IR (neat, cm -1 ): 2936, 2836, 1613, 1514, 1247.

Statistics shows that 702-23-8 is playing an increasingly important role. we look forward to future research findings about 2-(4-Methoxyphenyl)ethanol.

Reference:
Article; Karaki, Fumika; Kuwada, Miki; Tajiri, Saki; Kanda, Misaki; Yanai, Mari; Kamimura, Mitsuhiro; Itoh, Kennosuke; Fujii, Hideaki; Synthetic Communications; vol. 49; 2; (2019); p. 212 – 220;,
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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. 637031-88-0, name is 3,3-Difluorocyclobutanol. A new synthetic method of this compound is introduced below., COA of Formula: C4H6F2O

: A solution of 4′-bromo-6′- fluoro-r-(trifluoromethyl)spiro[l,3-dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine] (0809) (96.2mg, 0.2800mmol) and 2-(di-t-butylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-i-propyl-l,r- biphenyl (3.4 mg, 0.007 mmol) in l,4-dioxane (5.0 mL) was sparged with nitrogen for 3 mins. The reaction mixture was then treated sequentially with potassium hydroxide (47.3 mg, 0.84 mmol), water (101 pL, 5.62 mmol) and [2-(2-aminophenyl)phenyl]-methylsulfonyloxy- palladium; di-t-butyl-[3,6-dimethoxy-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (6.0 mg, 0.007 mmol) under continuous nitrogen stream. The vessel was sealed and heated to 80 C for 1 h and 30 min. The reaction mixture was quenched by the addition of acetic acid (64.3 pL, 1.13 mmol). The reaction mixture was poured into 75 mL of water and extracted with 4 x 20 mL EtOAc. The combined organics were dried with MgS04, filtered, and concentrated to dryness. The product was used without further purification (87 mg). During the reaction, some of the hydrodefluorinated product formed as an impurity. Data for 6-fluoro-l- (trifluoromethyl)-5,6-dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolan]-4-ol: LCMS ESI (+) (M+H) m/z 280. Data for l-(trifluoromethyl)-5,6- dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolan]-4-ol: LCMS ESI (+) (M+H) m/z 262.A solution of impure 6′-fluoro-r-(trifluoromethyl)spiro[l,3-dioxolane-2,7′- 5,6-dihydrocyclopenta[c]pyridine]-4′-ol (44.0 mg, 0.16 mmol), polymer supported (0812) triphenylphosphine (-2.06 mmol/g, 306.2 mg, 0.63 mmol), and 3,3-difluoro-cyclobutanol (68.1 mg, 0.63 mmol) in tetrahydrofuran (3.2 mL) was treated with diisopropyl (0813) azodicarboxylate (120 pL, 0.61 mmol) and stirred at 60 C for 2 h. The reaction mixture was filtered and the filter cake rinsed with 20 mL EtOAc. The filtrate was concentrated and purified by chromatography on silica using 10-30% EtO Ac/hexane to afford a clear solid (39.0 mg, 67%) that was a 2: 1 mixture of the fluorinated and hydrodefluorinated products. LCMS ESI (+) (M+H) m/z 370. Data for 4-(3,3-difluorocyclobutoxy)-6-fluoro-l- (trifluoromethyl)-5,6-dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolane]: LCMS ESI (+) (M+H) m/z 370. Data for 4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-5,6- dihydrospiro[cyclopenta[c]pyridine-7,2′-[l,3]dioxolane]: LCMS ESI (+) (M+H) m/z 352.A solution of impure 4′-(3,3-difluorocyclobutoxy)-6′-fluoro-r-(trifluoromethyl)spiro[l,3- dioxolane-2,7′-5,6-dihydrocyclopenta[c]pyridine] (39.0 mg, 0.106 mmol) in dichloromethane (2.0 mL) at 0 C was treated with perchloric acid (70% in water, 200 pL) and stirred at 0 C for 3 h. The reaction mixture was quenched by the addition of 5 mL of saturated aqueous (0817) NaHC03. The resulting mixture was extracted with 3 x 15 mL CH2Cl2. The combined organics were rinsed with 10 mL of brine, dried with MgS04, filtered, and concentrated to dryness. The product was used without further purification as a 2: 1 mixture of fluorinated and hydrodefluorinated ketones. LCMS ESI (+) (M+H) m/z 326. Data for 4-(3,3- difluorocyclobutoxy)-6-fluoro-l-(trifluoromethyl)-5,6-dihydro-7iT-cyclopenta[c]pyridin-7- one: LCMS ESI (+) (M+H) m/z 326. Data for 4-(3,3-difluorocyclobutoxy)-l- (trifluoromethyl)-5,6-dihydro-7i7-cyclopenta[c]pyridin-7-one: LCMS ESI (+) (M+H) m/z 308.A solution of impure 4-(3,3-difluorocyclobutoxy)-6-fluoro-l- (trifluoromethyl)-5,6-dihydrocyclopenta[c]pyridin-7-one (33.8 mg, 0.10 mmol) in dichloromethane (4.0 mL) was cooled to 0 C and sparged with nitrogen for 5 min. During this time formic acid (11.8 pL, 0.31 mmol) and triethylamine (28.8 pL, 0.21 mmol) were sequentially added. Once sparging was complete, RuCl(p-cymene)[(R,R)-Ts-DPEN] (1.3 mg, 0.002 mmol) was added under a continuous stream of nitrogen. The reaction vessel was sealed and placed into the refrigerator to react overnight. Volatiles were removed by concentration under reduced pressure. The residue was purified by chromatography on silica using 4-18% EtOAc/CH2Cl2 to afford ( 6R, 7L’)-4-(3 , 3 -difl uorocy d obutoxy )-6-fl uoro- 1 – (trifluoromethyl)-6,7-dihydro-5iT-cyclopenta[c]pyridin-7-ol (Compound 465) as a clear solid (5.4 mg, 16%) and (f?)-4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-6,7-dihydro-5i7- cyclopenta[c]pyridin-7-ol (Compound 466) as a clear solid (7.4 mg, 23%). Data for ( 6R,7S )- 4-(3, 3 -difl uorocycl obutoxy )-6-fluoro- l -(trifluoromethyl)-6,7-dihydro-5//- cyclopenta[c]pyridin-7-ol (Compound 465): Retention time HPLC (14 min) = 3.59 min; LCMS ESI (+) (M+H) m/z 328; 1H NMR (400 MHz, CDCl3): d 8.04 (s, 1H), 5.46-5.26 (m, 2H), 4.89-4.79 (m, 1H), 3.36-3.08 (m, 4H), 2.91-2.74 (m, 2H), 2.60 (dd, 1H). Data for (i?)-4-(3,3-difluorocyclobutoxy)-l-(trifluoromethyl)-6,7-dihydro-5iT-cyclopenta[c]pyridin-7- ol (Compound 466): Retention time HPLC (14 min) = 3.95 min; LCMS ESI (+) (M+H) m/z 310; 1H NMR (400 MHz, CDCI3): d 7.98 (s, 1H), 5.59-5.54 (m, 1H), 4.88-4.79 (m, 1H), 3.24- 3.07 (m, 3H), 2.89 (dd, 1H), 2.89-2.74 (m, 2H), 2.44-2.34 (m,…

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, 637031-88-0, 3,3-Difluorocyclobutanol.

Reference:
Patent; PELOTON THERAPEUTICS, INC.; JOSEY, John A.; SHRIMALI, Rajeev; WALLACE, Eli M.; WONG, Tai; (195 pag.)WO2019/191227; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7589-27-7, 2-(4-Fluorophenyl)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, Safety of 2-(4-Fluorophenyl)ethanol, blongs to alcohols-buliding-blocks compound. Safety of 2-(4-Fluorophenyl)ethanol

NaH 60percent suspension in mineral oil (2.400 g, equivalent to 1 .440 g of NaH, 60 mmol, 2 eq) was weighed into a flame-dried flask and suspended in dry D F (60 mL) with stirring, under a nitrogen atmosphere. To this was added 4 (4.205 g, 3.751 mL, 30 mL) and the temperature raised to 60 ¡ãC with stirring for 15 minutes. Chloroacetic acid (2.835 g, 30 mmol, 1 eq) was added to the flask and the mixture allowed to stir at 60 ¡ãC for a further 2.5 h. After cooling and removal of solvent, the residue was suspended in Et20 (30 mL) and extracted with water (2 x 30 mL). The combined aqueous layers were acidified with aqueous 2 HCI (to around pH 3) before extraction with EtOAc (3 x 30 mL). After removal of solvent, the crude solid was recrystallised from cyclohexane to yield 3.000g of pink crystals.

The synthetic route of 7589-27-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NOTTINGHAM; MISTRY, Shailesh; DARAS, Etienne; FROMONT, Christophe; JADHAV, Gopal; FISCHER, Peter Martin; KELLAM, Barrie; HILL, Stephen John; BAKER, Jillian Glenda; WO2012/4549; (2012); A1;,
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Related Products of 3360-41-6, 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.3360-41-6, name is 4-Phenylbutan-1-ol, molecular formula is C10H14O, molecular weight is 150.22, as common compound, the synthetic route is as follows.

The title compound can be prepared in a three-step process based on publication by Rong and Ruoho (1999). First, the alkoxide generated with NaH from 4-phenylbutanol can be alkylated with 1, 6-dibromohexane in presence of catalytic tetrabutylammonium bromide. The thus obtained bromide can be substituted by heating with sodium azide and catalytic sodium iodide in DMSO at 80C. The azide can then be reduced by hydrogenation in presence of palladium catalyst and di-t-butyl dicarbonate, obtaining the desired Boc-protected amine 23.

The chemical industry reduces the impact on the environment during synthesis 3360-41-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CORUS PHARMA; WO2005/63777; (2005); A1;,
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Application of 3597-91-9, 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. 3597-91-9, name is [1,1′-Biphenyl]-4-ylmethanol, molecular formula is C13H12O, 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.

Carbon tetrabromide (8.99 g, 27.1 mmol) and triphenyl phosphine (7.11 g, 27.1 mmol) wereadded to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 mmol) indichloromethane (100 ml_) at room temperature. Stirring was continued at room temperaturefor 1.5 hours then the solvent removed by evaporation under reduced pressure. Theresidue was purified by column chromatography on silica gel (1:20 diethyl ether:cyclohexane) to give the title compound (6.37g, 95%) as a white solid. 1H NMR (400 MHz:CDCI3): 7.6 (4 H), 7.45 (4 H), 7.35 (1 H), 4.55 (2 H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 3597-91-9, [1,1′-Biphenyl]-4-ylmethanol.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/110974; (2004); A1;,
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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.4170-90-5, name is Mesitylmethanol, molecular formula is C10H14O, molecular weight is 150.2176, as common compound, the synthetic route is as follows.Formula: C10H14O

A mixture of 1.50 g (0.01 mol) of 2,4,6-trimethylbenzyl alcohol, 1.00 g (0.01 mol) of succinic acid anhydride, 3.25 g (0.01 mol) of cesium carbonate, and 100 ml of dioxane was stirred at reflux temperature for 4 hours. The reaction mixture was cooled to room temperature and then filtered to remove the solid cesium carbonate. The solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel (acetone-hexane) to provide 1.167 g of succinic acid mono-(2,4,6-trimethylbenzyl) ester (46.62%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4170-90-5, Mesitylmethanol, and friends who are interested can also refer to it.

Reference:
Patent; SONUS PHARMACEUTICALS, INC.; US2007/142331; (2007); A1;,
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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. 124-76-5, name is Isoborneol. A new synthetic method of this compound is introduced below., Quality Control of Isoborneol

Example 8 Preparation of 1-[((1S)-endo)-(-)-bornyloxy]-5-(2-propenyl)-2-oxabicyclo[3.3.0]octane [(18a), (18b)] 16.9 parts of ((1S)-endo)-(-)-borneol (10) was added to a solution prepared by adding 21.0 parts of 2-(2-acetoxyethyl)-2-(2-propenyl)cyclopentanone (21) and 2.5 parts of pyridinium paratoluene sulfonate to 173 parts of toluene at room temperature. The mixture was stirred for 10 hours at 110C. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane: diethyl ether = 40: 1) to obtain 25.9 parts of the target isomer mixture. The isomer mixture was developed by silica gel thin layer chromatography using a 2:1 mixture of n-hexane and toluene as a developing solution to confirm that the Rf values were 0.28 (Isomer 9) and 0.36 (Isomer 10) when developed for 44 mm.

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, 124-76-5, Isoborneol.

Reference:
Patent; Zeon Corporation; EP1535917; (2005); A1;,
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Application of 39895-56-2, 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.39895-56-2, name is (4-(Aminomethyl)phenyl)methanol, molecular formula is C8H11NO, molecular weight is 137.179, as common compound, the synthetic route is as follows.

Furthermore, 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine (9a, Scheme 2; 0.588 g, 2.5 mmol),(4-(aminomethyl)phenyl)methanol (1 eq., 0.343 g, 2.5 mmol), and K2CO3 (1 eq., 0.343 g, 2.5 mmol)were combined in a flask. The solid material was dissolved in DMF (10 mL), and was stirred for 72 h atroom temperature (heated if necessary on the last day). Brine (100 mL) was added to the flask and theproduct was precipitated. The solid was filtered and dried overnight under high vacuum. The productwas purified using column chromatography (silica) with 50% ethyl acetate in hexanes as the eluent.White product (10b, Scheme 2) was produced (0.428 g, 1.28 mmol, 51%). 1H-NMR (300 MHz, CDCl3) delta 7.29 (m, 4H), 5.92 (s, 1H), 4.69 (s, 2H), 4.57 (d, J = 6.1 Hz, 2H), 3.79 (m, 4H), 3.69 (t, J = 4.6 Hz, 4H),1.88 (br s, 1H). 13C-NMR (101 MHz, DMSO-d6) delta 169.35, 168.74, 166.01, 165.66, 164.46, 164.32, 141.59,137.98, 137.93, 127.65, 127.30, 126.91, 126.87, 66.16, 63.15, 44.00, 43.95. Most 13C-NMR resonances showevidence of two conformers due to hindered rotation around the C-NHR bond.

The chemical industry reduces the impact on the environment during synthesis 39895-56-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Nelson, Ronald A; Schronce, Taylor; Huang, Yue; Albugami, Alanoud; Kulik, George; Welker, Mark E.; Molecules; vol. 23; 7; (2018);,
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