Category: 25662-28-6

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. 25662-28-6, name is Methyl 1-cyclopentene-1-carboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C7H10O2

EXAMPLE 20 2-(Piperidin-4-ylsulfanyl)cyclopentanecarboxylic acid methyl ester methyl 1-cyclopentene-1-carboxylate (0.24 ml) and Intermediate 12 (0.50 g) were dissolved in anhydrous methanol (20 ml), degassed with nitrogen, and cooled to -10 to -15 C. sodium bis(trimethylsilyl)amide, 1.0 M in tetrahydrofuran (1.93 ml) was added and the reaction stirred for 18 h, warming to room temperature.The reaction mixture was then evaporated and the residue partitioned between ethyl acetate (20 ml) and water (20 ml).The aqueous was extracted once more with ethyl acetate (10 ml) and the combined organic extracts were washed with 2% aqueous citric acid (20 ml), water (20 ml), saturated sodium bicarbonate (20 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure. The resultant amber oil was dissolved in dichloromethane (10 ml) and treated with trifluoroacetic acid (2 ml).After stirring at room temperature for 17 h, the solvents were evaporated and the residue azeotroped with 1:1 dichloromethane/hexane (3*20 ml).The residue was then dissolved in water (30 ml) and washed with diethyl ether (2*10 ml) before being basified with sodium carbonate to PH 11 and extracted with ethyl acetate (4*15 ml).The combined ethyl acetate extracts were then washed with saturated brine (10 ml), dried (Na2SO4) and reduced in vacuo to provide the title compound as a colourless gum (0.15 g, 31%). TLC Rf 0.26 (6% methanol/dichloromethane containing a trace of aqueous ammonia) MS 244 (MH+)

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Montana, John Gary; Baxter, Andrew Douglas; Owen, David Alan; Watson, Robert John; US2003/236416; (2003); A1;,
Ester – Wikipedia,
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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 25662-28-6 as follows. Safety of Methyl 1-cyclopentene-1-carboxylate

EXAMPLE 37; N-((lR)-l-{5-[5-chloro-3-fluoro-2-(2-methyl-2H-tetrazol-5-yl)phenyl]-3-fluoropyridin-2-yl}ethyl)-2- fluoro- 1 -hydroxy cyclopentanecarboxamide; Methyl cyclopent-1-ene-l-carboxylate (30.0 g, 237.8 mmol) was dissolved in 20 mL of dichloromethane and 3-chloroperbenzoic acid (64.4 g, 373.3 mmol) was added. The reaction was allowed to stir vigorously for 2 hours. The reaction mixture was diluted with EtOAc and washed with 0.5 NNuaOEta. The organic layer was dried over sodium sulfate, filtered and concentrated to give 48.0 grams of methyl 6-oxabicyclo[3.1.0]hexane-l-carboxylate. Methyl 6-oxabicyclo[3.1.0]hexane-l-carboxylate (2.10 g, 14.8 mmol) and N,N-diethyl- ethanamine trihydrofluoride (4.76 g, 29.5 mmol) were heated in a sealable Emrys microwave vessel with stir bar a microwave reactor at 180 0C for 30 minutes. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic layer was further washed with water and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated to a crude oil, which was subjected to chromatography on silica gel eluting with 0 to 25% EtOAc in hexanes to afford racemic trans methyl^-fluoro-l-hydroxycyclopentanecarboxylate.The racemic trans methyl-2-fluoro-l-hydroxycyclopentanecarboxylate (0.285 g, 1.76 mmol) was dissolved in 21.3 mL of a 4:1 solution of TEtaF:deionized water. A solution of 1 NNaOH was added to the reaction mixture, which was stirred for 1.5 hours. The reaction was acidified with 6 NHCl and extracted with EtOAc three times. The organic layers were combined, dried over sodium sulfate, filtered and concentrated to give racemic trans 2-fluoro-l-hydroxycyclopentanecarboxylic acid as a colorless oil.To a mixture of the compound of Reference Example 4 (0.215 g, 6.13 mmol), racemic trans 2-fluoro-l-hydroxycyclopentanecarboxylic acid (90.8 mg, 0.61 mmol), and (lH-l,2,3-benzotriazol- l-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (0.380 g, 0.86 mmol) in 3 mL of dichloromethane was added triethylamine (0.155 g, 1.53 mmol). This reaction mixture was allowed to stir at ambient temperature for 1 hour. The reaction mixture was washed with water, 0.25 NEtaC1, and EPO saturated aqueous sodium bicarbonate solution prior to drying over sodium sulfate. Filtration and solvent removal provided material which was subjected to chromatography on silica gel eluting with 0-40% EtOAc in hexanes to give a mixture of the two diastereomers. Subsequent preparatory TLC eluting with 40% EtOAc in hexanes yielded the title compound. Less polar diastereomer (beige solid): mass ion (ES+) of 481.0 for M+H+: 1H NMR (500 MHz, CDCI3) delta 8.11 (s, IH), 7.66 (bs, NH), 7.35 (d, J= 2.0Hz, IH)5 7.34-7.25 (m, 2H), 5.48 (quint, J= 6.8 Hz, IH), 4.71 (dd, J= 3.9 Hz, J= 53.0 Hz, IH), 4.33 (s, 3H), 4.20 (s, OH), 2.19-2.16 (m, 2H), 1.99-1.92 (m, 4H), 1.467 (d, J= 6.8 Hz, 3H). More polar diastereomer: mass ion (ES+) of 481.0 for M+H+-‘ 1H NMR (500 MHz, CDCI3) delta 8.13 (s, IH), 7.483 (bs,NH), 7.35 (d, J= 9.0 Hz, IH), 7.28-7.24 (m, 2H), 5.47 (m, IH), 4.79 (dd, J= 3.4 Hz, J= 53.0 Hz, IH), 4.34 (s, 3H), 4.23 (s, OH), 2.26-1.91 (m, 6H), 1.46 (d, J= 6.6 Hz, 3H).

According to the analysis of related databases, 25662-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/132837; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 25662-28-6 as follows. name: Methyl 1-cyclopentene-1-carboxylate

Example 1: Synthesis of compound of formula (IX) A solution of methyl- 1-cyclopentene-l -carboxylate (X) (10 mL, 81.88 mmol) in CH2C12 (200 mL) under N2 atmosphere is brought to 0C, and a solution of 1M DIBALH (diisobutylaluminium hydride) in hexane (204.7 mL, 204.7 mmol) is added drop by drop. The mixture is kept under stirring a 0C for 1 hour. H2O is added to the reaction, insolubles are filtered through celite, and the phases are separated. The organic phase is washed with brine, dried over Na2SO4, filtered and evaporated under low pressure. The pure compound of formula (IX) is obtained. Yield: 95% (7.62 g of a colourless liquid). Rf: 0.28 (EtPet/EtOAc 9: 1). ^- MR 400 MHz (CDC13) delta (ppm): 5.56 (s, 1H); 4.13 (s, 2H); 2.76 (bs, 1H); 2.30-2.26 (m, 4H); 1.90-1.82 (m, 2H). 13C-NMR 100 MHz (CDC13) delta (ppm): 143.67; 125.06; 61.60; 32.08; 31.86; 22.97. MS(ES+): m/z 121 [M+Na]+.

According to the analysis of related databases, 25662-28-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIPHARMA FRANCIS S.R.L.; TADDEI, Murizio; ATTOLINO, Emanuele; BALDUCCI, Evita; MICHIELETTI, Mario; WO2013/120871; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 25662-28-6, 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. 25662-28-6, name is Methyl 1-cyclopentene-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under nitrogen atmosphere, a mixture of in H2O (0.90muL, 0.050mmol) in THF (1mL) was added to an oven-dried reaction tube charged with (R)-H8-BINOL (22.1mg, 0.075mmol). After stirred at RT for 5min, Bu2Mg (1.0M in heptane, 50.0muL, 0.050mmol) and diarylphosphine oxide (3, 0.50mmol, 0.5M in anhydrous THF) were sequentially added and stirred for another 5min before being cooled to-20C. alpha,beta-Unsaturated ester (2, 0.50mmol) was then added, and the reaction was stirred at-20C for 2-3 days. The reaction mixture was quenched with sat. NH4Cl (2mL), diluted with H2O (5mL) and extracted with CH2Cl2 (10mL¡Á2). The combined organic phase was dried over anhydrous Na2SO4. After filtration and concentration, and the residue was purified by silica gel column chromatography (hexane: THF=5:1 to 1:1) to give the corresponding product. The enantiomeric excess was determined by the chiral HPLC analysis.

The synthetic route of Methyl 1-cyclopentene-1-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cao, Meng-Yue; Xu, Zhi-Min; Gao, Wei; Liu, Juan; Tan, Fen; Lu, Hai-Hua; Tetrahedron; vol. 75; 24; (2019); p. 3282 – 3291;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 25662-28-6, 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. 25662-28-6 name is Methyl 1-cyclopentene-1-carboxylate, This 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.

Experimental Procedures-Part 1 :; Step 1 – Oxidation of Carboxymethylcyclopentene:; Procedure:; To a cooled (00C) 2 L round bottom flask with a magnetic stir bar and internal temperature probe was added acetic anhydride (615 g, 570 mL, 6.02 mol). Chromium trioxide (214 g, 2.14 mol) was added in portions while maintaining constant stirring and to control the exotherm. The resulting blood red solution was stirred to dissolve the chromium trioxide until the temperature had cooled to 20 0C. A 5 L three-neck flask was fitted with an addition funnel, overhead stirring mechanism, nitrogen inlet and internal temperature probe and charged with 4 (100 g, 101 mL, 0.793 mol) in 1.4 L CH2Cl2. The oxidizing solution of chromium trioxide and acetic anhydride was charged to the addition funnel and added dropwise to the reaction mixture, maintaining the internal temperature between 10 and 14 0C. The initially yellow solution became dark after the first few drops of oxidizer were added.The reaction was worked up in two equally-sized batches due to limitations on vessel size in the laboratory. Each batch was treated exactly the same way, as follows: The dark, homogeneous solution was poured carefully into a 4 L beaker with an overhead stirring mechanism. The reaction flask was rinsed with 250 mL CH2Cl2. 500 mL H2O was added followed by 10 g NaHCC?3 which resulted in gas evolution. Additional NaHCC>3 (830 g, 10 mol) was added in portions while maintaining 500 rpm stir rate in the viscous mixture. The resulting dark green suspension was diluted with 1 L H2O and filtered through a 3 L fritted funnel containing a 1 cm pad of solka floe. The biphasic solution was extracted with CH2CI2 (3×1 L) and the combined organics dried using MgSO.), then filtered and the resulting solution was concentrated in vacuo to afford a pale green oil. Distillation through a 30 cm Vigreux column followed by recrystallization from MTBE:hexane (1:10, 55 mL total) provided 38.4 g of 5 as a white crystalline solid (35%).ted yield

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1-cyclopentene-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; BANYU PHARMACEUTICAL CO., LTD.; WO2008/21029; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 25662-28-6 name is Methyl 1-cyclopentene-1-carboxylate, This 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. 25662-28-6

To a stirred solution of methyl cyclopent-1-enecarboxylate (2.0 g, 15.89 mmol) in DCM (15.0 mL) was added (benzyl((trimethylsilyl)methyl)amino) methyl methanesulfonate (4.0 mL, 15.88 mmol) at rt and the mixture stirred at 0 C. for 15 min followed by the drop wise addition of trifluoroacetic acid (0.50 mL). The mixture was then stirred for 16 h at rt. After completion of reaction (by TLC), solvent was evaporated, water added (50.0 mL) followed by extraction with EtOAc (3¡Á100 mL) and the combined organic layer washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 7% EtOAc:hexane to obtain the product as a light yellow liquid (1.50 g, 75% yield). MS: 260.16 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 1-cyclopentene-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BIOTA EUROPE LTD.; US2012/88750; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics