ethyl decanoate

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:

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: The procedure is as in Example 20 for the preparation of ethyl n-decanoate, starting with (phenylthio)acetic acid (20 g) and 36N aqueous sulphuric acid solution (0.32 cc) in cyclohexanol (100 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent, cyclohexyl (phenylthio)acetate (29 g) is obtained, and is used in the crude state in the subsequent phases. After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: n-Decanoic acid (17.2 g), 36N aqueous sulphuric acid solution (3 cc) and ethanol (300 cc) are heated to boiling for 4 hours. After being cooled to a temperature in the region of 20° C., the solution is concentrated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa), and the residue is then taken up with dichloromethane (200 cc). The organic phase is washed with saturated aqueous sodium bicarbonate solution (2×100 cc), separated off after settling has taken place, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). Ethyl n-decanoate (18 g) is thereby obtained, and is used in the crude state in the subsequent syntheses. the solution is concentrated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa) The organic phase is washed with saturated aqueous sodium bicarbonate solution (2×100 cc) separated off after settling dried over anhydrous magnesium sulphate filtered concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: n-Decanoic acid (17.2 g), 36N aqueous sulphuric acid solution (3 cc) and ethanol (300 cc) are heated to boiling for 4 hours. After being cooled to a temperature in the region of 20° C., the solution is concentrated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa), and the residue is then taken up with dichloromethane (200 cc). The organic phase is washed with saturated aqueous sodium bicarbonate solution (2×100 cc), separated off after settling has taken place, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). Ethyl n-decanoate (18 g) is thereby obtained, and is used in the crude state in the subsequent syntheses. the solution is concentrated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa) The organic phase is washed with saturated aqueous sodium bicarbonate solution (2×100 cc) separated off after settling dried over anhydrous magnesium sulphate filtered concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)

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

実験手順: Ethyl n-decanoate (10 g) is added in the course of 10 minutes at a temperature in the region of -78° C. to a stirred mixture of diisopropylamine (5.6 cc), a 1.6M solution (37.5 cc) of n-butyllithium in hexane and tetrahydrofuran (30 cc). Stirring is maintained for 30 minutes at the same temperature, N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (14.3 g) is then added and stirring is maintained for 3 hours at a temperature in the region of -78° C. After a gradual warming to approximately 20° C., ammonium chloride (4 g) dissolved in water (50 cc) is added to the reaction medium. Dichloromethane (200 cc) and water (100 cc) are added, and the organic phase is separated off after settling has taken place. The aqueous phase is washed with dichloromethane (2×50 cc). The organic phases are combined, dried over anhydrous magnesium sulphate, filtered and evaporated at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is dissolved in a mixture (30 cc) of cyclohexane and ethyl acetate (60:40 by volume), and the solution obtained is poured onto silica (600 g) contained in a column 7 cm in diameter. Elution is performed with a mixture of cyclohexane and ethyl acetate (60:40 by volume), and the eluate is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). Ethyl 2-dimethylamino-5-ethoxycarbonyl-2,4-tridecadienoate (9.8 g) is thereby obtained, and is used in the crude state in the subsequent syntheses. is then added stirring After a gradual warming to approximately 20° C. is added to the reaction medium the organic phase is separated off after settling The aqueous phase is washed with dichloromethane (2×50 cc) dried over anhydrous magnesium sulphate filtered evaporated at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa) The residue is dissolved in a mixture (30 cc) of cyclohexane and ethyl acetate (60:40 by volume) the solution obtained is poured onto silica (600 g) Elution is performed with a mixture of cyclohexane and ethyl acetate (60:40 by volume) the eluate is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)

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

実験手順: The procedure is as in Example 20 for the preparation of ethyl n-decanoate, starting with (phenylthio)acetic acid (20 g) and 36N aqueous sulphuric acid solution (0.32 cc) in cyclohexanol (100 cc). After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent, cyclohexyl (phenylthio)acetate (29 g) is obtained, and is used in the crude state in the subsequent phases. After purification by chromatography on a silica column with a mixture of cyclohexane and ethyl acetate (70:30 by volume) as eluent

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: n-Decanoic acid (17.2 g), 36N aqueous sulphuric acid solution (3 cc) and ethanol (300 cc) are heated to boiling for 4 hours. After being cooled to a temperature in the region of 20° C., the solution is concentrated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa), and the residue is then taken up with dichloromethane (200 cc). The organic phase is washed with saturated aqueous sodium bicarbonate solution (2×100 cc), separated off after settling has taken place, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). Ethyl n-decanoate (18 g) is thereby obtained, and is used in the crude state in the subsequent syntheses. the solution is concentrated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa) The organic phase is washed with saturated aqueous sodium bicarbonate solution (2×100 cc) separated off after settling dried over anhydrous magnesium sulphate filtered concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: n-Decanoic acid (17.2 g), 36N aqueous sulphuric acid solution (3 cc) and ethanol (300 cc) are heated to boiling for 4 hours. After being cooled to a temperature in the region of 20° C., the solution is concentrated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa), and the residue is then taken up with dichloromethane (200 cc). The organic phase is washed with saturated aqueous sodium bicarbonate solution (2×100 cc), separated off after settling has taken place, dried over anhydrous magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). Ethyl n-decanoate (18 g) is thereby obtained, and is used in the crude state in the subsequent syntheses. the solution is concentrated to dryness at 50° C. under vacuum (20 mm Hg; 2.7 kPa) The organic phase is washed with saturated aqueous sodium bicarbonate solution (2×100 cc) separated off after settling dried over anhydrous magnesium sulphate filtered concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)

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

実験手順: Ethyl n-decanoate (10 g) is added in the course of 10 minutes at a temperature in the region of -78° C. to a stirred mixture of diisopropylamine (5.6 cc), a 1.6M solution (37.5 cc) of n-butyllithium in hexane and tetrahydrofuran (30 cc). Stirring is maintained for 30 minutes at the same temperature, N-(3-dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (14.3 g) is then added and stirring is maintained for 3 hours at a temperature in the region of -78° C. After a gradual warming to approximately 20° C., ammonium chloride (4 g) dissolved in water (50 cc) is added to the reaction medium. Dichloromethane (200 cc) and water (100 cc) are added, and the organic phase is separated off after settling has taken place. The aqueous phase is washed with dichloromethane (2×50 cc). The organic phases are combined, dried over anhydrous magnesium sulphate, filtered and evaporated at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is dissolved in a mixture (30 cc) of cyclohexane and ethyl acetate (60:40 by volume), and the solution obtained is poured onto silica (600 g) contained in a column 7 cm in diameter. Elution is performed with a mixture of cyclohexane and ethyl acetate (60:40 by volume), and the eluate is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). Ethyl 2-dimethylamino-5-ethoxycarbonyl-2,4-tridecadienoate (9.8 g) is thereby obtained, and is used in the crude state in the subsequent syntheses. is then added stirring After a gradual warming to approximately 20° C. is added to the reaction medium the organic phase is separated off after settling The aqueous phase is washed with dichloromethane (2×50 cc) dried over anhydrous magnesium sulphate filtered evaporated at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa) The residue is dissolved in a mixture (30 cc) of cyclohexane and ethyl acetate (60:40 by volume) the solution obtained is poured onto silica (600 g) Elution is performed with a mixture of cyclohexane and ethyl acetate (60:40 by volume) the eluate is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)