Category: 39590-81-3

Related Products of 39590-81-3 ,Some common heterocyclic compound, 39590-81-3, molecular formula is C5H10O2, 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.

1. Iodination of 6 to Prepare 7a: [0145] Triphenylphospine (257.2 g) and imidazole (66.7 g) were charged to a reactor. DCM (490 mL) was charged, agitation was initiated and the solution was cooled to 0 C. Iodine (249.2 g) was added as a solid portion-wise over 1 h while maintaining the internal temperature below 10 C. Upon completion of the addition, a solution of 6 (50 g) in DCM (113 mL) was slowly charged to the reactor over 0.5 h while maintaining the internal temperature below 10 C. After stirring for 2.5 h, an aqueous solution of NaCl (25 g) in water (225 mL) was charged to the reactor. Following phase separation, the bottom organic layer was diluted with n-heptane (550 mL). The organic phase was washed with an aqueous solution of sodium sulfite (21 g) in water (190 mL). Following layer separation, the organic phase was concentrated to 600 mL via vacuum distillation. Additional n-heptane (550 mL) was charged, and the mixture was again concentrated to 600 mL via vacuum distillation. The resulting slurry was filtered over a silica gel plug (85 g) that had been slurry packed with n-heptane. The silica gel plug was rinsed with additional n-heptane (1 L), and the filtrate was then concentrated via vacuum distillation to provide the desired product 7a as a colorless liquid (114 g, 70%). 1H NMR (400 MHz, CDCl3) delta 3.33 (s, 2H), 0.95 (s, 2H). 13C NMR (75 MHz, CDCl3): 19.1, 22.7, 26.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39590-81-3, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; Scott, Robert William; Vitale, Justin Philip; Matthews, Kenneth Stanley; Teresk, Martin Gerald; Formella, Alexandra; Evans, Jared Wayne; US2013/324740; (2013); A1;,
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Electric Literature of 39590-81-3, 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. 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane, molecular formula is C5H10O2, 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) [1-(tert-Butyldiphenylsilanyloxymethyl)cyclopropyl]methanol 1,1-Bis(hydroxymethyl)cyclopropane (2 g) and imidazole (6.67 g) were dissolved in N,N-dimethylformamide (100 mL) and the solution was ice-cooled. tert-Butyldiphenylchlorosilane (5.39 g) was added dropwise to the solution. Then, the reaction mixture was gradually heated to room temperature and stirred for 18 hours. tert-Butyl methyl ether and a saturated sodium chloride solution were added to the reaction mixture, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate. The drying agent was removed by filtration. The filtrate was concentrated under reduced pressure to obtain a residue. The residue was subjected to silica gel column chromatography (heptane-ethyl acetate) to obtain the title compound (2.62 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 0.30-0.40 (m, 2H), 0.45-0.53 (m, 2H), 1.07 (s, 9H), 2.56 (t, J=5.6 Hz, 1H), 3.61 (d, J=5.6 Hz, 2H), 3.62 (s, 2H), 7.35-7.46 (m, 6H), 7.64-7.70 (m, 4H).; (1) [1-(tert-Butyldiphenylsilanyloxymethyl)cyclopropyl]methanol 1,1-Bis(hydroxymethyl)cyclopropane (3.6 g) and imidazole (2.4 g) were dissolved in N,N-dimethylformamide (35 mL) in a nitrogen atmosphere. tert-Butylchlorodiphenylsilane (9.2 mL) was added to the solution at -15C, and the mixture was stirred at – 15C for one hour. Methanol and water were sequentially added to the reaction mixture, followed by extraction with ethyl acetate twice. The organic layers were sequentially washed with water and a saturated sodium chloride solution and dried over magnesium sulfate. The drying agent was removed by filtration and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to obtain the title compound (5.58 g). 1H-NMR (400 MHz, CDCl3) delta(ppm): 0.34-0.38 (m, 2H), 0.47-0.51 (m, 2H), 1.06 (s, 9H), 2.57 (t, J=5.6 Hz, 1H), 3.61 (d, J=5.6 Hz, 2H), 3.62 (s, 2H), 7.35-7.45 (m, 6H), 7.64-7.68 (m, 4H).

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 39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2017275; (2009); A1;,
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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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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. 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane, the common compound, a new synthetic route is introduced below. Application In Synthesis of 1,1-Bis(Hydroxymethyl)cyclopropane

(0236) To a stirred solution of (1-hydroxymethyl-cyclopropyl)-methanol (Combi-blocks, 10.0 g, 97.9 mmol) and triethylamine (22.0 g, 220 mmol) in DCM (120 mL) at -5 C. was added thionyl chloride (13.0 g, 110 mmol) dropwise over 30 min. The resulting suspension was stirred at -5 C. for an additional 2 h and then diluted with water (100 mL). The organic phase was separated, washed with brine, dried over sodium sulfate and filtered. The filtrate was dried under reduced pressure to give 5,7-dioxa-6-thia-spiro[2.5]octane 6-oxide as a white solid (13.5 g, 93%). 1HNMR (CDCl3, 300 MHz): delta 5.26-5.30 (d, 2H, J=11.4 Hz), 3.06-3.10 (d, 2H, J=11.7 Hz), 0.84-0.89 (m, 2H), 0.49-0.54 (m, 2H).

The synthetic route of 39590-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HUDSON BIOPHARMA INC.; Chen, Yi; Ding, Qingjie (Jack); Sun, Yang-sheng; US2015/322076; (2015); A1;,
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Reference of 39590-81-3, Adding some certain compound to certain chemical reactions, such as: 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane,molecular formula is C5H10O2, 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 39590-81-3.

General procedure: The diol (48 mmol, 1 eq) wasdissolved into DMF (120 mL) under argon. At 0C NaH (1.1 eq, 60% in mineral oil) was added inone portion and the mixture was stirred at 0C during 45 min. BnBr (0.97 eq) was added dropwise,the mixture was allowed to warm at room temperature and stirred overnight. The reaction wasquenched with saturated NH4Cl solution (20 mL) and then diluted with water. The crude mixturewas extracted with Et2O and the organic layer was washed with brine, dried over anhydrous MgSO4,filtered and concentrated in vacuo. Benzylated compound was then purified by flashchromatography on silica gel.

According to the analysis of related databases, 39590-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chalopin, Thibaut; Jebali, Khaoula; Gaulon-Nourry, Catherine; Denes, Fabrice; Lebreton, Jacques; Mathe-Allainmat, Monique; Tetrahedron; vol. 72; 2; (2016); p. 318 – 327;,
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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.39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane, molecular formula is C5H10O2, molecular weight is 102.13, as common compound, the synthetic route is as follows.HPLC of Formula: C5H10O2

Into a solution of [l-(hydroxymethyl)cyclopropyl]methanol (9.5 g, 93.02 mmol,) and CC14 (15.57 g, 102.43 mmol) in THF (50 mL) at 0 C was added [bis(dimethylamino)phosphanyl]-dimethylamine (16.70 g, 102.33 mmol). The resulting solution was stirred overnight at room temperature and then quenched by the addition of water. The resulting solution was extracted with DCM and the organic layers combined. The resulting mixture was washed with sat. NaCl and dried over Na2S04 and then concentrated. The residue was purified by chromatography (EtO Ac/pet. ether (1 : 1) to afford 5.2 g (46%) of [1- (chloromethyl)cyclopropyl]methanol as yellow oil.

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; PRINCIPIA BIOPHARMA INC.; BRAMELD, Kenneth Albert; VERNER, Erik; (122 pag.)WO2016/191172; (2016); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane. This compound has unique chemical properties. The synthetic route is as follows. 39590-81-3

A. Iodination of Diol 6 to Prepare 7a [0228] Triphenylphospine (257.2 g) and imidazole (66.7 g) were charged to a reactor. DCM (490 mL) was charged, agitation was initiated and the solution was cooled to 0 C. Iodine (249.2 g) was added as a solid portion-wise over 1 h while maintaining the internal temperature below 10 C. Upon completion of the addition, a solution of 6 (50 g) in DCM (113 mL) was slowly charged to the reactor over 0.5 h while maintaining the internal temperature below 10 C. After stirring for 2.5 h, an aqueous solution of NaCl (25 g) in water (225 mL) was charged to the reactor. Following phase separation, the bottom organic layer was diluted with n-heptane (550 mL). The organic phase was washed with an aqueous solution of sodium sulfite (21 g) in water (190 mL). Following layer separation, the organic phase was concentrated to 600 mL via vacuum distillation. Additional n-heptane (550 mL) was charged, and the mixture was again concentrated to 600 mL via vacuum distillation. The resulting slurry was filtered over a silica gel plug (85 g) that had been slurry packed with n-heptane. The silica gel plug was rinsed with additional n-heptane (1 L), and the filtrate was then concentrated via vacuum distillation to provide the desired product 7a as a colorless liquid (114 g, 70%). 1H NMR (400 MHz, CDCl3) delta 3.33 (s, 2H), 0.95 (s, 2H). 13C NMR (75 MHz, CDCl3): 19.1, 22.7, 26.0.

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, 39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane.

Reference:
Patent; Scott, Robert William; Wang, Fang; Shi, Bing; Mogalian, Erik; US2013/324496; (2013); A1;,
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39590-81-3, 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 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane. This compound has unique chemical properties. The synthetic route is as follows.

a) [1-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]methyl]-cyclopropylmethanol To a solution of 3-(2-cyanophenylsulfonyloxy)-5-methylphenol (1.45 g, 5.0 mmol), as prepared in the step a of example 13), tri-n-butylphosphine (1.62 g, 8.0 mmol) and 1,1-dihydroxymethylcyclopropane (1.52 g, 15 mmol), as prepared in U.S. Patent No. 5,472,964, in anhydrous tetrahydrofuran (50 mL) was added 1,1′-(azodicarbonyl)dipiperidine (2.02, 8.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (80 mL) was added to the mixture, and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (10% ethyl acetate in dichloromethane) to give the title compound as a white solid (1.15, 62%). 1H-NMR (300 MHz, CDCl3) delta 8.09 (m, 1H), 7.93 (m, 1 H), 7.80 (m, 2H), 6.66 (s, 1H), 6.60 (s, 1H), 6.56 (s, 1H), 3.86 (s, 2H), 3.60 (s, 2H), 2.26 (s, 3H), 1.85 (br s, 1H), 0.62 (s, 4H).

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 39590-81-3, 1,1-Bis(Hydroxymethyl)cyclopropane.

Reference:
Patent; Ortho-McNeil Pharmaceutical, Inc.; EP906091; (2006); B1;,
Alcohol – Wikipedia,
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A common compound: 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane,molecular formula is C5H10O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 39590-81-3

To (5 volumes) of dichloro methane was charged a solution of imidazole and triphenylphosphine. The resultant reaction mixture was cooled to about 0C. Then added a solution of iodine in dichloro methane (5 volumes) at about 0C for about 60 mm.. Thenadded a solution of cyclopropane- 1,1 -diyldimethanol in dichloro methane (5 volumes) at about 0C for about 30 mm. and stirred at 10-15C for about 3 hrs. Then the reaction mass was diluted with brine solution at 10-15C. The organic and aqueous layers were separated and to the organic layer n-heptane (10 volumes) was charged. The total organic layer was washed with saturated sodium sulphite solution (2 times). 70 % of the organic layer wasdistilled at below 45C under vacuum. Then (10 volumes) of n-heptane was added and 12 volumes of the solvent was distilled at below 45C under vacuum. The slurry was filtered on silica bed and washed with n-heptane, the filterate mls were distilled below 45C under vacuum to yield the title compound. Yield: 46%

With the rapid development of chemical substances, we look forward to future research findings about 39590-81-3.

Reference:
Patent; GRANULES INDIA LIMITED; VETUKURI, Prasada Raju Vnkv; GILLA, Goverdhan; RAPOLU, Rajesh Kumar; CHIGURUPATI, Krishna Prasad; (54 pag.)WO2016/103232; (2016); 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.39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane, molecular formula is C5H10O2, molecular weight is 102.13, as common compound, the synthetic route is as follows.39590-81-3

5 g of cyclopropane-1,1-diyldimethanol are solubilized in 31 mL of pyridine. Cooling is performed down to 0-5 C., and then 10.3 mL of mesyl chloride are added dropwise, stirring is performed for 2 h. Add 40.46 mL of H2O+12.24 mL of concentrated HCl in order to precipitate the compound. The precipitate is filtered and dried in the oven. 10 g (yield=80%) of cyclopropane-1,1-diylbis(methylene)dimethanesulfonate are obtained as a white powder:

Statistics shows that 39590-81-3 is playing an increasingly important role. we look forward to future research findings about 1,1-Bis(Hydroxymethyl)cyclopropane.

Reference:
Patent; SANOFI; Arigon, Jerome; Brollo, Maurice; Clement, Jacques; Combet, Romain; Durand, Florence; El Ahmad, Youssef; Labrosse, Jean-Robert; Letallec, Jean-Philippe; Ronan, Baptiste; US2013/289031; (2013); A1;,
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