3-diethoxyphosphorylpropanenitrile

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: A mixture of diethyl[3-(N-phthalimido)]propylphosphonate (ex. 5) (3.72 g; 11.4 mmoles), absolute ethanol (46 ml) and hydrazine hydrate (0.78 ml of 98% purity; 15.7 mmoles) is stirred at reflux for 35 min. The mixture is filtered and the solvent is distilled under vacuo. The resulting oil is dissolved in CHCl3 (10 ml) and is filtered again. Solvent removal in vacuo gives a colorless liquid (0.7 g; yield 30%). According to example 4, diethyl 3-aminopropylphosphonate (6) is also obtained from diethyl 2-cyanoethylphosphonate in an analogous fashion followed by vacuum distillation at about 115° C. and 0.18 mbar (yield 80%). at reflux for 35 min The mixture is filtered the solvent is distilled under vacuo The resulting oil is dissolved in CHCl3 (10 ml) is filtered again Solvent removal in vacuo gives a colorless liquid (0.7 g; yield 30%)

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

実験手順: Sodium hydride (ca. 60%, 1.0 g, 28.1 mmol) was suspended in tetrahydrofuran (12 ml), and a solution of diethyl cyanoethylphosphonate (4.7 g, 26.8 mmol) in tetrahydrofuran (12 ml) was added thereto under ice cooling condition. The reaction mixture was stirred for 1 hr. A solution of 2-pyridinecarbaldehyde (2.7 g, 25.0 mmol) in tetrahydrofuran (10 ml) was added to the mixture, and the mixture was stirred at 0° C. to room temperature for 6 hrs. The reaction mixture was combined with water under ice cooling condition, concentrated to the half amount and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (100 g) column chromatography. The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected and concentrated to give Z-form of the titled compound (0.50 g, 15%). And simultaneously, the fractions eluted with hexane-ethyl acetate (3:2, v/v) were collected and concentrated to give E-form of the titled compound. the mixture was stirred at 0° C. to room temperature for 6 hrs concentrated to the half amount extracted with ethyl acetate The organic layer was washed with saturated brine dried over magnesium sulfate The solvent was evaporated The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected concentrated

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

実験手順: Sodium hydride (ca. 60%, 1.0 g, 28.1 mmol) was suspended in tetrahydrofuran (12 ml), and a solution of diethyl cyanoethylphosphonate (4.7 g, 26.8 mmol) in tetrahydrofuran (12 ml) was added thereto under ice cooling condition. The reaction mixture was stirred for 1 hr. A solution of 2-pyridinecarbaldehyde (2.7 g, 25.0 mmol) in tetrahydrofuran (10 ml) was added to the mixture, and the mixture was stirred at 0° C. to room temperature for 6 hrs. The reaction mixture was combined with water under ice cooling condition, concentrated to the half amount and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (100 g) column chromatography. The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected and concentrated to give Z-form of the titled compound (0.50 g, 15%). And simultaneously, the fractions eluted with hexane-ethyl acetate (3:2, v/v) were collected and concentrated to give E-form of the titled compound. the mixture was stirred at 0° C. to room temperature for 6 hrs concentrated to the half amount extracted with ethyl acetate The organic layer was washed with saturated brine dried over magnesium sulfate The solvent was evaporated The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected concentrated

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

実験手順: A mixture of diethyl[3-(N-phthalimido)]propylphosphonate (ex. 5) (3.72 g; 11.4 mmoles), absolute ethanol (46 ml) and hydrazine hydrate (0.78 ml of 98% purity; 15.7 mmoles) is stirred at reflux for 35 min. The mixture is filtered and the solvent is distilled under vacuo. The resulting oil is dissolved in CHCl3 (10 ml) and is filtered again. Solvent removal in vacuo gives a colorless liquid (0.7 g; yield 30%). According to example 4, diethyl 3-aminopropylphosphonate (6) is also obtained from diethyl 2-cyanoethylphosphonate in an analogous fashion followed by vacuum distillation at about 115° C. and 0.18 mbar (yield 80%). at reflux for 35 min The mixture is filtered the solvent is distilled under vacuo The resulting oil is dissolved in CHCl3 (10 ml) is filtered again Solvent removal in vacuo gives a colorless liquid (0.7 g; yield 30%)

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

実験手順: A mixture of diethyl[3-(N-phthalimido)]propylphosphonate (ex. 5) (3.72 g; 11.4 mmoles), absolute ethanol (46 ml) and hydrazine hydrate (0.78 ml of 98% purity; 15.7 mmoles) is stirred at reflux for 35 min. The mixture is filtered and the solvent is distilled under vacuo. The resulting oil is dissolved in CHCl3 (10 ml) and is filtered again. Solvent removal in vacuo gives a colorless liquid (0.7 g; yield 30%). According to example 4, diethyl 3-aminopropylphosphonate (6) is also obtained from diethyl 2-cyanoethylphosphonate in an analogous fashion followed by vacuum distillation at about 115° C. and 0.18 mbar (yield 80%). at reflux for 35 min The mixture is filtered the solvent is distilled under vacuo The resulting oil is dissolved in CHCl3 (10 ml) is filtered again Solvent removal in vacuo gives a colorless liquid (0.7 g; yield 30%)

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

実験手順: Sodium hydride (ca. 60%, 1.0 g, 28.1 mmol) was suspended in tetrahydrofuran (12 ml), and a solution of diethyl cyanoethylphosphonate (4.7 g, 26.8 mmol) in tetrahydrofuran (12 ml) was added thereto under ice cooling condition. The reaction mixture was stirred for 1 hr. A solution of 2-pyridinecarbaldehyde (2.7 g, 25.0 mmol) in tetrahydrofuran (10 ml) was added to the mixture, and the mixture was stirred at 0° C. to room temperature for 6 hrs. The reaction mixture was combined with water under ice cooling condition, concentrated to the half amount and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (100 g) column chromatography. The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected and concentrated to give Z-form of the titled compound (0.50 g, 15%). And simultaneously, the fractions eluted with hexane-ethyl acetate (3:2, v/v) were collected and concentrated to give E-form of the titled compound. the mixture was stirred at 0° C. to room temperature for 6 hrs concentrated to the half amount extracted with ethyl acetate The organic layer was washed with saturated brine dried over magnesium sulfate The solvent was evaporated The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected concentrated

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

実験手順: Sodium hydride (ca. 60%, 1.0 g, 28.1 mmol) was suspended in tetrahydrofuran (12 ml), and a solution of diethyl cyanoethylphosphonate (4.7 g, 26.8 mmol) in tetrahydrofuran (12 ml) was added thereto under ice cooling condition. The reaction mixture was stirred for 1 hr. A solution of 2-pyridinecarbaldehyde (2.7 g, 25.0 mmol) in tetrahydrofuran (10 ml) was added to the mixture, and the mixture was stirred at 0° C. to room temperature for 6 hrs. The reaction mixture was combined with water under ice cooling condition, concentrated to the half amount and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was subjected to a silica gel (100 g) column chromatography. The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected and concentrated to give Z-form of the titled compound (0.50 g, 15%). And simultaneously, the fractions eluted with hexane-ethyl acetate (3:2, v/v) were collected and concentrated to give E-form of the titled compound. the mixture was stirred at 0° C. to room temperature for 6 hrs concentrated to the half amount extracted with ethyl acetate The organic layer was washed with saturated brine dried over magnesium sulfate The solvent was evaporated The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected concentrated

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

実験手順: A mixture of diethyl[3-(N-phthalimido)]propylphosphonate (ex. 5) (3.72 g; 11.4 mmoles), absolute ethanol (46 ml) and hydrazine hydrate (0.78 ml of 98% purity; 15.7 mmoles) is stirred at reflux for 35 min. The mixture is filtered and the solvent is distilled under vacuo. The resulting oil is dissolved in CHCl3 (10 ml) and is filtered again. Solvent removal in vacuo gives a colorless liquid (0.7 g; yield 30%). According to example 4, diethyl 3-aminopropylphosphonate (6) is also obtained from diethyl 2-cyanoethylphosphonate in an analogous fashion followed by vacuum distillation at about 115° C. and 0.18 mbar (yield 80%). at reflux for 35 min The mixture is filtered the solvent is distilled under vacuo The resulting oil is dissolved in CHCl3 (10 ml) is filtered again Solvent removal in vacuo gives a colorless liquid (0.7 g; yield 30%)