2-methyloctanoyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Next, 2.02 g (11.4 mmol) of the above (+)-2-methyl octanoyl chloride and 3 ml of nitrobenzene were cooled to 0° C. in a flask and added with 3.06 g (22.9 mmol) of anhydrous aluminum chloride with stirring, which were stirred at room temperature for 30 minutes. Thereafter, 2.89 g (7 mmol) of (+)-biphenyl-2-methyloctanoate biphenyl dissolved in 3 ml of nitrobenzene was added thereto, which was reacted by stirring at room temperature for 140 hours. After the completion of the reaction, 2 normal hydrochloric acid and ice were added and extracted with chloroform. The extract was washed with water, dried on anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified through a column chromatography of silica gel to obtain 1.55 g (yield: 49%) of an oily (+)-4-(2-methyloctanoyl) biphenyl-2-methyloctanoate. which were stirred at room temperature for 30 minutes was added which was reacted by stirring at room temperature for 140 hours were added extracted with chloroform The extract was washed with water dried on anhydrous magnesium sulfate distilled to remove the solvent The residue was purified through a column chromatography of silica gel

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Next, 2.02 g (11.4 mmol) of the above (+)-2-methyl octanoyl chloride and 3 ml of nitrobenzene were cooled to 0° C. in a flask and added with 3.06 g (22.9 mmol) of anhydrous aluminum chloride with stirring, which were stirred at room temperature for 30 minutes. Thereafter, 2.89 g (7 mmol) of (+)-biphenyl-2-methyloctanoate biphenyl dissolved in 3 ml of nitrobenzene was added thereto, which was reacted by stirring at room temperature for 140 hours. After the completion of the reaction, 2 normal hydrochloric acid and ice were added and extracted with chloroform. The extract was washed with water, dried on anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified through a column chromatography of silica gel to obtain 1.55 g (yield: 49%) of an oily (+)-4-(2-methyloctanoyl) biphenyl-2-methyloctanoate. which were stirred at room temperature for 30 minutes was added which was reacted by stirring at room temperature for 140 hours were added extracted with chloroform The extract was washed with water dried on anhydrous magnesium sulfate distilled to remove the solvent The residue was purified through a column chromatography of silica gel

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Then, 2.38 g (19.0 mmol) of thionyl chloride was maintained at a temperature of 36°~38° C. in a flask, to which was added dropwise 2.51 g (15.9 mmol) of the above (+)-2-methyl octanoic acid over 7 minutes with stirring. After the reaction with stirring at room temperature for 40 minutes, the reaction was further continued by stirring at a temperature of 80° C. for 30 minutes. Then, the reaction product was distilled to obtain 2.81 g (15.9 mmol, yield: 100%) of a colorless and transparent (+)-2-methyl octanoyl chloride. After the reaction with stirring at room temperature for 40 minutes by stirring at a temperature of 80° C. for 30 minutes Then, the reaction product was distilled

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To this solution was added dropwise 2.61 g (10.1 mmol) of the above 4-bromobenzyl-(1-ethoxy) ethyl ether over 40 minutes. After the completion of the addition, the mixture was heated under reflux for 1 hour and cooled to -78° C., to which was added dropwise 1.70 g (9.6 mmol) of (+)-2-methyl octanoic acid chloride dissolved in 20 ml of tetrahydrofuran over 40 minutes. The mixture was stirred at -78° C. for 3 hours and gradually turned to room temperature. It was added with 10 ml of a normal hydrochloric acid cooled at 0° C. and stirred for 1 hour. The product was extracted with ether and washed with a saturated aqueous solution of sodium hydrogen carbonate and further a saturated aqueous solution of sodium chloride. It was dried on anhydrous magnesium sulfate, and the oily matter after the removal of solvent was purified by a column chromatography of silica gel to obtain 323 mg (yield 14 %) of a colorless and oily 4-(2-methyloctanoyl) benzyl alcohol. After the completion of the addition the mixture was heated under reflux for 1 hour gradually turned to room temperature cooled at 0° C. stirred for 1 hour The product was extracted with ether washed with a saturated aqueous solution of sodium hydrogen carbonate It was dried on anhydrous magnesium sulfate the oily matter after the removal of solvent was purified by a column chromatography of silica gel

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To this solution was added dropwise 2.61 g (10.1 mmol) of the above 4-bromobenzyl-(1-ethoxy) ethyl ether over 40 minutes. After the completion of the addition, the mixture was heated under reflux for 1 hour and cooled to -78° C., to which was added dropwise 1.70 g (9.6 mmol) of (+)-2-methyl octanoic acid chloride dissolved in 20 ml of tetrahydrofuran over 40 minutes. The mixture was stirred at -78° C. for 3 hours and gradually turned to room temperature. It was added with 10 ml of a normal hydrochloric acid cooled at 0° C. and stirred for 1 hour. The product was extracted with ether and washed with a saturated aqueous solution of sodium hydrogen carbonate and further a saturated aqueous solution of sodium chloride. It was dried on anhydrous magnesium sulfate, and the oily matter after the removal of solvent was purified by a column chromatography of silica gel to obtain 323 mg (yield 14 %) of a colorless and oily 4-(2-methyloctanoyl) benzyl alcohol. After the completion of the addition the mixture was heated under reflux for 1 hour gradually turned to room temperature cooled at 0° C. stirred for 1 hour The product was extracted with ether washed with a saturated aqueous solution of sodium hydrogen carbonate It was dried on anhydrous magnesium sulfate the oily matter after the removal of solvent was purified by a column chromatography of silica gel

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Next, 2.02 g (11.4 mmol) of the above (+)-2-methyloctanoic acid chloride and 3 ml of nitrobenzene were charged into a flask, and cooled to 0° C., to which was added 3.06 g (22.9 mmol) of anhydrous aluminum chloride with stirring and then the resulting mixture was stirred at room temperature for 30 minutes. This mixture was added with a solution of 2.89 g (7 mmol) of (+)-2-methyloctanoic acid biphenyl dissolved in 3 ml of nitrobenzene, which was reacted at room temperature for 140 hours with stirring. After the completion of the reaction, 2N hydrochloric acid and ice were added, and the extraction with chloroform was carried out, and the extract was washed with water, dried on anhydrous magnesium sulfate, distilled to remove the solvent, and purified by a column chromatography of silica gel to obtain 1.55 g (yield 49%) of an oily (+)-2-methyloctanoic acid-4-(2-methyloctanoyl) biphenyl. the resulting mixture was stirred at room temperature for 30 minutes which was reacted at room temperature for 140 hours with stirring were added the extraction with chloroform the extract was washed with water dried on anhydrous magnesium sulfate distilled to remove the solvent purified by a column chromatography of silica gel

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Next, 2.02 g (11.4 mmol) of the above (+)-2-methyloctanoic acid chloride and 3 ml of nitrobenzene were charged into a flask, and cooled to 0° C., to which was added 3.06 g (22.9 mmol) of anhydrous aluminum chloride with stirring and then the resulting mixture was stirred at room temperature for 30 minutes. This mixture was added with a solution of 2.89 g (7 mmol) of (+)-2-methyloctanoic acid biphenyl dissolved in 3 ml of nitrobenzene, which was reacted at room temperature for 140 hours with stirring. After the completion of the reaction, 2N hydrochloric acid and ice were added, and the extraction with chloroform was carried out, and the extract was washed with water, dried on anhydrous magnesium sulfate, distilled to remove the solvent, and purified by a column chromatography of silica gel to obtain 1.55 g (yield 49%) of an oily (+)-2-methyloctanoic acid-4-(2-methyloctanoyl) biphenyl. the resulting mixture was stirred at room temperature for 30 minutes which was reacted at room temperature for 140 hours with stirring were added the extraction with chloroform the extract was washed with water dried on anhydrous magnesium sulfate distilled to remove the solvent purified by a column chromatography of silica gel

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Then, 2.38 g (19.0 mmol) of thionyl chloride was charged into a flask and maintained at a temperature of 36°~38° C., to which was added dropwise 2.15 g (15.9 mmol) of the above (+)-2-methyloctanoic acid in 7 minutes with stirring. The resulting mixture was stirred at room temperature for 40 minutes and at a temperature of 80° C. for 30 minutes. Then, the reaction product was distilled to obtain 2.81 g (15.9 mmol, yield 100%) of a colorless and transparent (+)-2-methyloctanoic acid chloride. maintained at a temperature of 36°~38° C., to which The resulting mixture was stirred at room temperature for 40 minutes and at a temperature of 80° C. for 30 minutes Then, the reaction product was distilled

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Then, 8.93 g (56.4 mmol) of the above (+)-2-methyl octanoic acid was added to 8.98 g (75.5 mmol) of thionyl chloride placed in a flask with stirring at room temperature. Thereafter, the reaction was carried out at room temperature for 10 minutes, at 30° C. for 20 minutes, at 40° C. for 30 minutes and at 70° C. for 2 hours with stirring. After the excessive amount of thionyl chloride was distilled off, there was obtained 9.80 g (55.5 mmol, yield 98%) of light brown (+)-2-methyl octanoic acid chloride. placed in a flask with stirring After the excessive amount of thionyl chloride was distilled off

反応条件: temp:0.00; pressure:0.00; stir: