Category: 1559-02-0

A common compound: 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, belongs to esters-buliding-blocks compound, 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. 1559-02-0

Example 91 2″-amino-6′-(5-chloropyrid-3-yl)-l”-methyldispiro[cyclopropane-l,3′-chroman-4′,4″- imidazol]-5′(l’H)-oneStep A: A mixture of diethyl cyclopropane-l,l-dicarboxylate (14.1 mL, 80.6 mmol) and lithium tri-tert- butoxyaluminohydride (201.4 mL, 201.4 mmol) was heated to reflux in THF for 3 hours. The mixture was cooled down and partitioned between water and EtOAc. The organics were washed with water, brine and dried with Na2S04. This was concentrated down and then purified on a column using 10 to 50% EtOAc:hexanes to give ethyl l-(hydroxymethyl)cyclopropanecarboxylate (1.5 g, 10.4 mmol, 12.9%) as an 12.9%) as an oil.

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, 1559-02-0, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; HUNT, Kevin, W.; RIZZI, James, P.; COOK, Adam; WO2011/72064; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 1559-02-0, 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. 1559-02-0 name is Diethyl 1,1-cyclopropanedicarboxylate, 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.

To 500 ml of a three-necked flask was added 200 ml of methanol and 30 g of 1,1-cyclopropanedicarboxylic acid diethyl ester, cooled to 10 C, stir A solution of sodium hydroxide (NaOH 6.4 g, water 32 ml) was added dropwise, The reaction was carried out at room temperature for 3 hours, the reaction was terminated, the solvent was distilled off under reduced pressure, A white solid. To the solid was added 200 ml of water and 150 ml of ethyl acetate, ] Stir and layer, discard the organic phase. The aqueous layer was adjusted to pH 3 to 4 with 2 mol / L hydrochloric acid, Ethyl acetate extraction (200 ml x 2), The organic phase was dried over anhydrous sodium sulfate, filtered, The solvent was distilled off under reduced pressure, To give a colorless translucent oil

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

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhao Rui; Li Xinlu; Meng Qingyi; Zhang Xiquan; Shi Xiangfei; (25 pag.)CN103965104; (2017); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1559-02-0, 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. 1559-02-0 name is Diethyl 1,1-cyclopropanedicarboxylate, 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.

General procedure: Diethyl cyclopropane-1,1-dicarboxylatederivatives (1.0 eq.) were dissolved in EtOH. KOH (1.0 eq.)in ethanol solution was added and stirred for 5 h. After the completion of the reaction, the intermediatewas dissolved in THF solution at 15 C. 4-Methylmorpholine (1.2 eq.), isobutyl chloroformate(1.0 eq.) and 4-amino-2-fluorophenol (1.0 eq.) were added. The crude product was purified by columnchromatography, and the above process was repeated. The final product compounds 12 were obtained.

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

Reference:
Article; Jiang, Yingnan; Zhang, Ke; Gao, Suyu; Wang, Guihua; Huang, Jian; Wang, Jinhui; Chen, Lixia; Molecules; vol. 21; 5; (2016);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, A new synthetic method of this compound is introduced below., name: Diethyl 1,1-cyclopropanedicarboxylate

Synthesis of 1-(ethoxycarbonyl)cyclopropanecarboxylic acid Diethyl 1, 1-cyclopropane dicarboxylate (20g) was hydrolyzed in IN NaOH (107 m4) and ethanol (220D) for 16 hours, and the ethanol was removed by distillation under reduced pressure. The remaining starting material was removed by using ethyl acetate and the aqueous layer was acidified by IN HCI. The reaction mixture was extracted with ethyl acetate and distilled under reduced pressure. The residue was purified by silica gel column to give the title compound in a yield of 94%. 1H NMR(CDCl3) No. 1.06 (t, 3H), 1.53 (m, 2H), 1.62 (m, 2H), 4.21 (q, 2H) ESI: 159 +1) +C7H1004

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; ANADYS PHARMACEUTICALS, INC.; WO2005/79812; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H14O4

(a) 1-Ethoxycarbonylcyclopropanecarboxylic acid (1a) A solution of sodium hydroxide (2.15 g, 54 mmol) in water (15 ml) was added dropwise to a stirred solution of diethyl 1,1-cyclopropanedicarboxylate (10 g, 54 mmol) in ethanol (30 ml) while the temperature was maintained below 25 C. After the completion of the addition, the resulting mixture was stirred at room temperature for 60 hours. Most of ethanol was removed by evaporation in vacuo and the residue was diluted with brine, acidified with 6N hydrochloric acid and extracted with diethyl ether. The extract was dried over magnesium sulfate, filtered and concentrated. The residue was purified by distillation to give the title compound (bp 66-9 C./0.15 mm) as a viscous oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1559-02-0.

Reference:
Patent; Merck & Co., Inc.; US4766145; (1988); A;,
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 1559-02-0 as follows. SDS of cas: 1559-02-0

Synthesis of 1-Hydroxymethyl-cyclopropanecarboxylic acid ethyl ester A solution of lithium aluminum-tri-tert-butoxyhydride 1.0M in THF (28.5 mL, 28.5 mmol) is added to a solution of diethyl 1,1-cyclopropanedicarboxylate (2.0 mL, 11.4 mmol) in anhydrous THF (85.0 mL). After stirring the reaction mixture for 4 h, 10 mL of lithium aluminum-tri-tert-butoxyhydride 1.0M solution in THF is added and the solution is stirred for 18 h. The reaction mixture is diluted with DCM, washed with 1N aqueous HCl solution, saturated aqueous NaHCO3 solution and brine. After drying the organic phase over anhydrous Na2SO4, removal of the solvent under reduced pressure affords 1.60 g of 1-hydroxymethyl-cyclopropanecarboxylic acid ethyl ester that is used in the next step without further purification. Yield: 85%. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.88 (2H, q, J=4.1 Hz), 1.21-1.33 (5H, m), 2.59 (1H, t, J=6.9 Hz), 3.63 (2H, d, J=7.2 Hz), 4.17 (2H, q, J=7.1 Hz).

According to the analysis of related databases, 1559-02-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2010/76029; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Diethyl 1,1-cyclopropanedicarboxylate

To a stirred solution of diethyl cyclopropane-1, 1-dicarboxylate (2.13 g, 11.4 mmol) in THF (80 mL) at RT, lithium aluminum tri-tert-butoxyhydride (38.76 mL, 38.76 mmol, 1.0 M solution in THF) was added slowly. After the addition was completed, the reaction mixture was stirred at RT for 18 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with IN aq HCI (20 mL), water (20 mL), 5% aq. NaHC03 (25 mL), brine (20 mL), dried over anhydrous Na2S04, filtered and concentrated to afford the title compound (1.3 g, 79%, yellow oil). *H NMR (400 MHz, CDCI3) : delta = 4.20- 4.13(m, 2H), 3.62 (m, 2H), 2.61 (m, 1H), 1.29-1.24 (m, 5H), 0.88-0.85 (m, 2H) ppm.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1559-02-0.

Reference:
Patent; LEO PHARMA A/S; NIELSEN, Simon Feldbaek; LARSEN, Jens Christian H¡ãjland; WO2013/92739; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 1559-02-0, These common heterocyclic compound, 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, 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.

To a mixture of diethyl 1 ,1-cyclopropanedicarboxylate (10.0 g, 53.7 mmol) in ethanol (70 mL) and water (35 mL) was added sodium hydroxide (2.1 g, 53.7 mmol). The reaction was stirred at 25 C for 16 h and diluted with ethyl acetate (60 mL). The organic layer was discarded. The aqueous phase was adjusted to pH = 3 by addition of aqueous hydrochloric acid (4 M). The mixture was extracted with ethyl acetate (3 x 80 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate and concentrated under reduced pressure to give crude 1- ethoxycarbonylcyclopropanecarboxylic acid (6.6 g, 78%) as a colorless oil. NMR (400MHz, CDCl3) delta 12.86 (br s, 1H), 4.31 – 4.17 (m, 2H), 1.87 – 1.81 (m, 2H), 1.77 – 1.69 (m, 2H), 1.32 – 1.24

The synthetic route of 1559-02-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1559-02-0, 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 1559-02-0 as follows.

In the 2L three-mouth reaction bottle,Add 255.3 g of diethyl 1,1-cyclopropanedicarboxylate,840mL EtOH,The ice water bath cools it to 0 C.Slowly add 137.32g KHCO3The temperature control is added below 30 C.Naturally rise to room temperature,Stir the reaction for 15 h,TLC monitors the reaction completely,Add 1L of water,Extracted with (PE: EA = 1:1) 300 mL ¡Á 2,Remove the organic phase,Concentrated HCl adjusts pH=2,Extracted with EA 370mL¡Á2,Take the organic phase,Desolvent1,1-cyclopropanedicarboxylic acid monoethyl ester 201.7 g,The yield was 93%.

According to the analysis of related databases, 1559-02-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wuhan Institute of Technology; Huang Qimao; Feng Jinjin; Gao Hui; (13 pag.)CN105111155; (2018); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

1559-02-0, 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. 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 64 Preparation of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate A 1M solution of lithium aluminum tri-tert-butoxyhydride in tetrahydrofuran (70.90 mL, 70.90 mmol) was added to a stirred solution of diethyl cyclopropane-1,1′-dicarboxylate (6 g, 32.20 mmol) in tetrahydrofuran (129 mL) at 23 C. The resulting solution was heated to 65 C. and stirred for 24 h. The cooled reaction mixture was diluted with a 10% solution of sodium bisulfate (275 mL) and extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a pale yellow oil (4.60, 91%): 1H NMR (300 MHz, CDCl3) delta 4.16 (q, J=7 Hz, 2H), 3.62 (s, 2H), 2.60 (br s, 1H), 1.22-1.30 (m, 5H), 0.87 (dd, J=7, 4 Hz, 2H).

The synthetic route of 1559-02-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel I.; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank J.; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter; (118 pag.)US2016/60245; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics