Category: 15224-11-0

These common heterocyclic compound, 15224-11-0, name is Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate, 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. HPLC of Formula: C7H12O3

Di-terf-butyl azodicarboxylate (4.8 g, 20.809 mmol) was added portionwise to a solution of 3-methoxy-5-nitrophenol [7145-49-5] (3.2 g, 18.917 mmol), ethyl 2-(hydroxymethyl)cyclopropanecarboxylate 6a (3 g, 20.809 mmol), and PP i3 (5.46 g, 20.809 mmol) in THF (150 mL). The reaction was stirred at room temperature under N2 for 18 h. The solution was concentrated under reduced pressure. The crude residue was purified by preparative LC (irregular SiOH 20-45 muetatauiota, 220 g, heptane/EtOAc from 85/15 to 75/25). The pure fractions were combined and concentrated under reduced pressure to give methyl 2-((3-methoxy-5- nitrophenoxy)methyl)cyclopropanecarboxylate 6b (1 .4 g).

The synthetic route of Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BONFANTI, Jean-Francois; KESTELEYN, Bart, Rudolf, Romanie; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; COESEMANS, Erwin; FORTIN, Jerome, Michel, Claude; MERCEY, Guillaume, Jean, Maurice; RABOISSON, Pierre, Jean-Marie, Bernard; (153 pag.)WO2018/215315; (2018); A1;,
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. 15224-11-0, name is Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate

EXAMPLE 40 ethyl 2-{[4-chloro-2-({[(5-cyano-2-pyrazinyl)amino]carbonyl}amino)phenoxy]methyl}cyclopropanecarboxylate The desired product (2.5 mg, 6%) was prepared by substituting ethyl 2-(hydroxymethyl)cyclopropanecarboxylate (14.4 mg, 0.10 mmol) for 2-cyclohexen-1-ol in Example 1. MS (ESI(-)) m/z 414 (M-H)-; 1H NMR (500 MHz, DMSO-d6) delta 10.95 (s, 1H), 10.20 (br s, 1H), 8.91 (s, 1H), 8.77 (s, 1H), 8.24-8.28 (m, 1H), 7.04-7.11 (m, 2H), 4.12-4.18 (m, 1H), 3.96-4.08 (m, 3H), 1.82-1.92 (m, 1H), 1.73-1.79 (m, 1H), 1.10-1.19 (m, 4H), 1.02-1.08 (m, 1H).

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; Li, Gaoquan; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Sham, Hing L.; Wang, Gary T.; US2004/259885; (2004); A1;,
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. 15224-11-0, name is Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 15224-11-0

General Procedure 61 Ethyl 2-[(4-bromo-1H-pyrazol-1-yl)methyl]cyclopropanecarboxylate (4-3): To a reaction solution of ethyl 2-(hydroxymethyl)cyclopropanecarboxylate (4-1) (577 mg; 4.0 mmol) with Et3N (1.1 mL; 8.0 mmol) and DMAP (49 mg; 0.4 mmol) in 12 mL of CH2Cl2 at 0 C. was added methanesulfonyl chloride (0.4 mL; 4.8 mmol). The resulting mixture of brown color suspension was stirred at 0 C. to room temperature under N2 for overnight. The reaction mixture was quenched with NaHCO3, then partitioned between CH2Cl2 (200 mL) and saturated NaHCO3 solution (50 mL); brine (50 mL). The organic layer was dried (Na2SO4), then filtered through silica gel pad, eluted with hexane:EtOAc/1:1. The filtrate was concentrated by vacuum to give 880 mg of ethyl 2-{[(methylsulfonyl)oxy]methyl}cyclopropanecarboxylate as a yellow oil (99% yield). 1H NMR (400 MHz, chloroform-D) delta ppm 0.91-1.02 (m, 1H) 1.26 (q, J=6.99 Hz, 3H) 1.29-1.36 (m, 1H) 1.63-1.74 (m, 1H) 1.79-1.92 (m, 1H) 3.02 (s, 3H) 3.99-4.24 (m, 4H).

The synthetic route of 15224-11-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (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 15224-11-0 as follows. category: esters-buliding-blocks

Step 2: Ethyl 2-((methylsulfonyloxy)methyl)cyclopropanecarboxylate (C-6) To a solution of alcohol C-5 (0.50 g, 3.47 mmol) and triethylamine (1.45 mL, 10.41 mmol) in anhydrous methylene chloride (12.0 mL) at 0 C. was added methanesulfonic anhydride (0.908 g, 5.21 mmol) in one portion. The reaction mixture was then stirred at room temperature for 1 h, diluted with diethyl ether (50 mL) and quenched with an aqueous pH 7 phosphate buffer solution (30 mL). The aqueous layer was extracted with diethyl ether (2*50 mL). The combined organic extracts were then successively washed with an aqueous pH 7 phosphate buffer solution (70 mL) and brine (70 mL), dried over MgSO4, filtered, and concentrated to give ethyl 2-((methylsulfonyloxy)methyl)cyclopropanecarboxylate (C-6) as a colorless oil (0.698 g, 91% yield). This material was immediately placed under argon and dissolved with anhydrous DMF (1.57 mL) to give a 2.0 M stock solution, which was used as such for the next step.

According to the analysis of related databases, 15224-11-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ting, Pauline C.; Aslanian, Robert; Caplen, Mary Ann; Cao, Jianhua; Chan, Tin-Yau; Kim, David; Kim, Hyunjin; Kim, Jae-Hun; Kuang, Rongze; Lee, Joe F.; Schwerdt, John; Wu, Heping; Zorn, Nicolas; US2011/224137; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics