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. 13380-85-3, name is Methyl 4-(hydroxymethyl)cyclohexanecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C9H16O3
In a nitrogen atmosphere, 10.0 g of the compound represented by Formula (I-105-1), 6.0 g of triethylamine, and 40 mL of tetrahydrofuran were added to a reaction container. While the resulting mixture was cooled with ice, 6.4 g of ethyl chloroformate was added dropwise to the mixture. The mixture was then stirred at room temperature for one hour. The precipitate was filtered away. In a nitrogen atmosphere, 2.2 g of sodium borohydride and 10 mL of tetrahydrofuran were added to another reaction container. While the resulting mixture was cooled with ice, the filtrate prepared above was added dropwise to the mixture. A liquid mixture of 40 mL of methanol and 10 mL of water was added dropwise to the mixture. The mixture was subsequently stirred at room temperature for three hours. After 20 mL of 10%-hydrochloric acid had been added to the mixture, extraction was performed with ethyl acetate. Then, purification was performed by column chromatography (silica gel, hexane/ethyl acetate). Hereby, 7.4 g of the compound represented by Formula (I-105-2) was prepared. (0129) In a nitrogen atmosphere, 7.4 g of the compound represented by Formula (I-105-2), 4.1 g of pyridine, and 35 mL of dichloromethane were added to a reaction container. While the resulting mixture was cooled with ice, 5.4 g of methanesulfonyl chloride was added dropwise to the mixture. The mixture was subsequently stirred at room temperature for three hours. The mixture was poured into water and then washed with 5%-hydrochloric acid and subsequently with a saline solution. Then, purification was performed by column chromatography (silica gel, hexane/ethyl acetate) and recrystallization (acetone/hexane). Hereby, 7.5 g of the compound represented by Formula (I-105-3) was prepared. (0130) In a nitrogen atmosphere, 25.0 g of the compound represented by Formula (I-105-4), 100 mL of acetic acid, and 100 mL of 48%-hydrobromic acid were added to a reaction container. The resulting mixture was heated to reflux for 12 hours. After the mixture had been cooled, it was poured into 1 L of water. Subsequently, extraction was performed with ethyl acetate, and washing was then performed with a saline solution. After the solvent had been distilled away, the remaining acetic acid was removed as an azeotrope with toluene. Then, purification was performed by column chromatography (alumina, ethyl acetate). Hereby, 12.0 g of the compound represented by Formula (I-105-5) was prepared. (0131) In a nitrogen atmosphere, 2.1 g of the compound represented by Formula (I-105-5), 7.5 g of the compound represented by Formula (I-105-3), 6.2 g of potassium carbonate, and 70 mL of N,N-dimethylformamide were added to a reaction container. The resulting mixture was stirred for 3 days while being heated at 90 C. The mixture was then poured into water. Subsequently, extraction with toluene and washing with a saline solution were performed. Then, purification was performed by column chromatography (silica gel, toluene) and recrystallization (toluene/hexane). Hereby, 4.8 g of the compound represented by Formula (I-105-6) was prepared. (0132) In a nitrogen atmosphere, 4.8 g of the compound represented by Formula (I-105-6), 20 mL of tetrahydrofuran, 20 mL of methanol, and 10 mL of a 25%-aqueous sodium hydroxide solution were added to a reaction container. The resulting mixture was stirred for 2 hours while being heated at 60 C. After the solvent had been distilled away, the residue was again dissolved in a mixed solvent of tetrahydrofuran and water. To the resulting solution, 10%-hydrochloric acid was added such that the pH of the solution became 2. After the solvent had been distilled away, water was added to the residue to precipitate a solid, which was filtered. The solid was washed with water and then dried. Hereby, 4.0 g of the compound represented by Formula (I-105-7) was prepared. (0133) To a reaction container, 15.0 g of the compound represented by Formula (I-105-8), 17.7 g of the compound represented by Formula (I-105-9), 16.0 g of potassium carbonate, and 100 mL of N,N-dimethylformamide were added. The resulting mixture was stirred for 12 hours while being heated at 80 C. After the mixture had been cooled and then diluted with dichloromethane, washing was performed with water and subsequently with a saline solution. Then, purification was performed by column chromatography (alumina, dichloromethane). Hereby, 24.2 g of the compound represented by Formula (I-105-10) was prepared. (0134) To a reaction container, 24.2 g of the compound represented by Formula (I-105-10), 60 mL of tetrahydrofuran, 60 mL of methanol, and 1 mL of concentrated hydrochloric acid were added. The resulting mixture was stirred at room temperature for eight hours. After the solvent had been distilled away, the residue was diluted with ethyl acetate. Subsequently, washing was performed with water and then with a saline solution. Then, purification was performed by column chromatography (alumina, ethyl acetate) and recr…
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; DIC Corporation; Kadomoto, Yutaka; Horiguchi, Masahiro; Koiso, Akihiro; (109 pag.)US2018/2276; (2018); A1;,
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