Tag: M.W=100-200

Synthetic Route of 112-27-6 , The common heterocyclic compound, 112-27-6, name is 2,2′-(Ethane-1,2-diylbis(oxy))diethanol, molecular formula is C6H14O4, 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.

Compound 6-1 (235 g, 1.57 mol) was dissolved in 500 mL of tetrahydrofuran, then potassium hydroxide (41.2 g, 0.57 mmol, 82% w/w) was added, and then p-toluenesulfonyl chloride 6-2 (100 g, 0.52 mol) was added in batches, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into 1200 mL of water, and extracted with ethyl acetate (400 mL*3). The extract liquid was combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure and purified by silica gel column chromatography, with an eluent (petroleum ether:ethyl acetate=1:1), to obtain the target product 6-3 (118 g, 75%) as a colorless oil. LC-MS: m/z=305[M+H]+.

The synthetic route of 112-27-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen China Resources Gosun Pharmaceutical Co., Ltd.; Jiang, Xiongjie; Huang, Quanhua; Yang, Zhanao; (43 pag.)US2017/2028; (2017); 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.403-41-8, name is 1-(4-Fluorophenyl)ethyl Alcohol, molecular formula is C8H9FO, molecular weight is 140.16, as common compound, the synthetic route is as follows.SDS of cas: 403-41-8

Dissolve 1-(4-fluorophenyl)ethanol (1.24 g, 8.85 mmol) in n-hexane (29.5 mL),CAL-B (195 mg), vinyl acetate (1.60 mL, 17.7 mmol) and triethylamine (0.0710 mL, 0.885 mmol) were added.The reaction mixture was stirred at room temperature for 12 hours. The mixture was filtered to remove impurities and reduced pressure to remove solvent. The mixture was purified by silica gel column chromatography (n-hexane / EtOAc = 8: 1, Rf = 0.25 (n-hexane / EtOAc = 4: 1)) and purified.(S)-1-(4-fluorophenyl)ethan-1-ol (574 mg, 46%) was obtained as a colorless oil (Formula 9)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,403-41-8, 1-(4-Fluorophenyl)ethyl Alcohol, and friends who are interested can also refer to it.

Reference:
Patent; ERICA Industry-University Cooperation Foundation of Hanyang University; Min Seon-jun; Kim Ju-hyeon; Chu Hyeon-a; Cho Yong-seo; Lee Jae-gyun; Bae Ae-nim; (23 pag.)KR2019/115976; (2019); 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. 13807-89-1, name is 2-((4-Methoxybenzyl)oxy)ethanol, molecular formula is C10H14O3, 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. Safety of 2-((4-Methoxybenzyl)oxy)ethanol

Dissolve 3.7ml of oxalyl chloride in dichloromethane (75ml) and control the temperature to -70 C.Dissolve dimethyl sulfoxide (6.4 ml) in dichloromethane (10 ml) and slowly dropwise.After completion of the dropwise addition, the reaction was performed for 1 hour.6 g (33.0 mmol) of 2- (4-methoxybenzyloxy) ethanol was dissolved in dichloromethane (5 ml) and slowly added. After two hours of reaction, triethylamine (12.5 ml) was slowly added dropwise.After 30 minutes of reaction, the temperature reduction device was removed and the temperature was raised to zero degrees.3N HCl was added slowly, extracted, and the organic layers were combined. With 1N HCl,Saturated sodium bicarbonate solution, washed with saturated brine, dried,The organic solvent was spin-dried to obtain 5 g of product.

With the rapid development of chemical substances, we look forward to future research findings about 13807-89-1.

Reference:
Patent; Nanjing Gurui Biological Technology Co., Ltd.; Mei Yan; (56 pag.)CN110734456; (2020); 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. 2009-83-8, name is 6-Chlorohexan-1-ol, molecular formula is C6H13ClO, 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 C6H13ClO

Chlorohexanol (71.9 mmol, 10.00 g), p-nitrophenol (86.4 mmol, 11.80 g), K2CO3 (109 mmol, 15.09 g), KI (5 mg), and DMF (80 mL) were added to a three-necked flask and refluxed at 120 C.After 6 hours of reaction, samples were taken for gas chromatography.When there is no peak of 6-chloro-1-hexanol in the gas phase, the reaction is stopped, and the mixed solution is poured into a large amount of water to obtain an off-white precipitate. After drying,Recrystallization from ethanol gave p-nitrophenoxyhexanol (Intermediate A) with a yield of about 87%.The purity by HPLC analysis was 95.2%.

With the rapid development of chemical substances, we look forward to future research findings about 2009-83-8.

Reference:
Patent; Changzhou University; Xue Xiaoqiang; Liang Kang; Jiang Bibiao; Huang Wenyan; Yang Hongjun; Jiang Qimin; Jiang Li; (20 pag.)CN110343079; (2019); A;,
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Related Products of 4152-92-5 ,Some common heterocyclic compound, 4152-92-5, molecular formula is C8H11NO, 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.

General procedure: Step i: Ketone 1 (1 mmol), primary amine 2 (1 mmol), and a mixture of Ti(Oi-Pr)4 (3.1 mg, 1.1 mol%) in 1-(trimethylsilyl)-2-pyrrolidinone (393 mg, 2.5 mmol) were heated at 70C with shaking in a sealed vial for 6 h. Step ii: After cooling down to r.t., EtOH (2 mL) was added to the solution and it was shaken until homogenization followed by the addition of NaBH4 (68 mg, 1.8 mmol). The resulting heterogeneous mixture was left staying overnight at r.t. Then, H2O (2 mL) was added and the mixture was sonicated for 2 h at r.t. to decompose the excess of NaBH4. The product was extracted with CHCl3 (3 mL), and the organic phase was washed with H2O (3 × 7 mL), dried (Na2SO4), and evaporated to give the respective secondary amine 3. Samples with purity below 95% as determined by LC-MS or 1H NMR spectroscopy were further purified by column chromatography (SiO2,eluent A: CHCl3, eluent B: i-PrOH, a linear gradient from 0% eluent B to 100% eluent B was used).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4152-92-5, its application will become more common.

Reference:
Article; Bogolubsky, Andrey V.; Moroz, Yurii S.; Pipko, Sergey E.; Panov, Dmitriy M.; Konovets, Anzhelika I.; Doroschuk, Roman; Tolmachev, Andrey; Synthesis; vol. 46; 13; (2014); p. 1765 – 1772;,
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Related Products of 637031-88-0, 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.

: 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,637031-88-0, its application will become more common.

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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Related Products of 29055-08-1, 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.29055-08-1, name is (2-(Methylamino)phenyl)methanol, molecular formula is C8H11NO, molecular weight is 137.179, as common compound, the synthetic route is as follows.

[00263] To a solution of 2-(N-methylamino)-benzylalcohol(b) (536 mg, 3.9 mmol) in dry dichloromethane (25 ml) and diisopropylethylamine (681 mul, 3.9 mmol) was added dropwise chloromethyl chloroformate (360 mul, 4.0 mmol) and the reaction mixture was stirred at 0° C. with occasional check of the reaction progress by t.l.c (n-hexane:ethyl acetate=2:1). After 2 h, the starting material disappeared on t.l.c and the solution was used directly for the following reaction. [00264] Step 2 [00265] To the reaction mixture were added diisopropylethylamine (900 mul, 5.0 mmol) and acetic anhydride (400 mg) and stirred for 3 h at ambient temperature. The reaction mixture was partitioned with dichloromethane (50 ml) and water (30 ml). The water layer was separated and extracted again with dichloromethane (50 ml). The combined organic layer was washed with brine (30 ml.x.2), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting yellowish oil was purified on a column of silica gel (wakogel C-200 10 g, eluent dichloromethane_methanol=200:1) to give the title compound(c) as colorless syrup (740 mg, 70percent). EI-MS: m/z 271(M+); 1H-NMR (270 MHz, CDCl3): delta 2.10 (3H, s), 3.30 (3H, s), 5.07-5.78 (2H, br.d), 5.60 (0.8H, d, J=5.9), 5.73 (0.8H, d, J=5.9), 5.85 (0.4H, br.s), 7.16-7.23 (1H, m), 7.37-7.49 (3H, m).

Statistics shows that 29055-08-1 is playing an increasingly important role. we look forward to future research findings about (2-(Methylamino)phenyl)methanol.

Reference:
Patent; Basilea Pharmaceutica AG; US6812238; (2004); B1;,
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Related Products of 37585-16-3 , The common heterocyclic compound, 37585-16-3, name is (2-Amino-4-chlorophenyl)methanol, molecular formula is C7H8ClNO, 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.

B. N-(Benzylcarbonyl)-5-chloro-2-hydroxymethylaniline To a suspension of 5-chloro-2-hydroxymethyl aniline (8.00 g) in dichloromethane (400 ml) under nitrogen at room temperature, was added triethylamine (15.6 ml). The reaction mixture was cooled to 0 C. then phenyl acetyl chloride (14.80 ml) was added dropwise over 10 mins, and the reaction mixture was allowed to warm to room temperature and stir for 2 h. The mixture was washed with 1N HCl (2*250 ml) and brine (1*250 ml). The aqueous layers were re-extracted using CH2 Cl2 (1*250 ml) and the combined organic layers were dried (MgSO4), filtered and the solvent was removed under vacuum to leave an orange solid. The solid was suspended in MeOH (400 ml), sodium hydroxide (2.20 g) was added in water (100 ml) and the reaction mixture was allowed to stir under gentle heating (50 C.) for 45 mins. The methanol was removed in vacuo, then the aqueous residue was extracted with dichloromethane (1*200 ml) and the organic layer was washed with brine (1*150 ml) and saturated sodium hydrogen carbonate solution (1*150 ml). The organic layer was dried (MgSO4), filtered and the solvent was removed under vacuum to leave a solid. Trituration with diethyl ether gave the required compound (10.00 g).

The synthetic route of 37585-16-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck, Sharp & Dohme Ltd.; US5614532; (1997); A;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5259-98-3, name is 5-Chloropentan-1-ol, the common compound, a new synthetic route is introduced below. Safety of 5-Chloropentan-1-ol

5-chloro-l-pentanol (12,26 g, 0,1 mol) was dissolved in dry dichloromethane (400 mL). 3,4-Dihydro-2H-pyrane (12,62 g, 0,15 mol) and pyridine toluene-4-sulphonate (1,26 g, 5 mmol) was then added and the reaction mixture was stirred magneti- cally in a nitrogen atmosphere at room temperature over night. Sodium-hydrogen-carbonate, saturated solution (150 mL) was added and the phases were separated. The aqueous phase was then extracted with dichloromethane (4 x 25 mL). The com- bined dichloromethane phases were washed with water (2 x 20 mL) and then dried (MGS04). Dichloromethane was then dis- tilled out on a rotary evaporator and yielded 19,6 g (95 percent) of a pale yellow oil. NMR indicated a pure product.

The synthetic route of 5259-98-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AXIMED AS; WO2005/25314; (2005); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 62285-58-9, name is (2,6-Dimethylphenyl)methanol, the common compound, a new synthetic route is introduced below. Computed Properties of C9H12O

[0484] To a solution of (2,6-dimethyl-phenyl)-methanol (13.6 g, 100.00 mmol) in DCM (400 mL) was added PBr3 (5.7 g, 150.0 mmol) and pyridine (0.5 mL). The mixture was stirred at 0 C for 2 hrs. TLC showed the reaction was completed. The reaction was quenched with slow addition of ice water (50 mL). The aqueous phase was extracted with DCM (300 mL x3). The organic layer was washed with brine (500 mL), dried over Na2S04 and concentrated to give 2-bromom ethyl- 1,3 -dimethyl -benzene (19.1 g, yield: 96 %) as a yellow solid.

The synthetic route of 62285-58-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; SMITH, Layton H.; PINKERTON, Anthony B.; HERSHBERGER, Paul; MALONEY, Patrick; MCANALLY, Danielle; (167 pag.)WO2019/32720; (2019); A1;,
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