2-cyclohexylideneacetonitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 10 l round-bottom flask is loaded with 285 g (4.57 mols) of 90% potassium hydroxide in flakes and 1775 ml of hexane. The mixture is heated to 55° C. and, keeping heating, a solution consisting of 450 g (4.59 mols) of cyclohexanone and 1351 ml of acetonitrile is quickly dropped therein (during the addition temperature falls to 52.6° C.). The mixture is refluxed for 7 hours, then cooled at room temperature. 2863 ml of water are added thereof to dissolve the solid. The organic phase is washed twice with water (1000 ml each). The phases are separated and the organic phase is evaporated to dryness under vacuum, to obtain 462 g of a residue which is distilled under 10 mmHg at 100-105° C. keeping heating is quickly dropped falls to 52.6° C. The mixture is refluxed for 7 hours cooled at room temperature to dissolve the solid The organic phase is washed twice with water (1000 ml each) The phases are separated the organic phase is evaporated to dryness under vacuum

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 10 l round-bottom flask is loaded with 285 g (4.57 mols) of 90% potassium hydroxide in flakes and 1775 ml of hexane. The mixture is heated to 55° C. and, keeping heating, a solution consisting of 450 g (4.59 mols) of cyclohexanone and 1351 ml of acetonitrile is quickly dropped therein (during the addition temperature falls to 52.6° C.). The mixture is refluxed for 7 hours, then cooled at room temperature. 2863 ml of water are added thereof to dissolve the solid. The organic phase is washed twice with water (1000 ml each). The phases are separated and the organic phase is evaporated to dryness under vacuum, to obtain 462 g of a residue which is distilled under 10 mmHg at 100-105° C. keeping heating is quickly dropped falls to 52.6° C. The mixture is refluxed for 7 hours cooled at room temperature to dissolve the solid The organic phase is washed twice with water (1000 ml each) The phases are separated the organic phase is evaporated to dryness under vacuum

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

実験手順: The nitrile (compound 2, 0.78 g, 6.44 mmol), nitromethane (0.80 g, 13.11 mmol) and tetrabutyl ammonium fluoride (1.0 M in tetrahydrofuran, 10 mL, 10 mmol) were heated in 20 mL tetrahydrofuran to 70° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1 to give the required product as a yellow oil (0.83 g, 71%). washed with dilute hydrochloric acid and water dried over magnesium sulphate filtered evaporated to dryness The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1

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

実験手順: The nitrile (compound 2, 0.78 g, 6.44 mmol), nitromethane (0.80 g, 13.11 mmol) and tetrabutyl ammonium fluoride (1.0 M in tetrahydrofuran, 10 mL, 10 mmol) were heated in 20 mL tetrahydrofuran to 70° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1 to give the required product as a yellow oil (0.83 g, 71%). washed with dilute hydrochloric acid and water dried over magnesium sulphate filtered evaporated to dryness The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1

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

実験手順: Sodium hydride (60% in oil, 0.80 g, 20 mmol) was suspended in 50 mL tetrahydrofuran and chilled in ice under nitrogen. Diethylcyanomethyl phosphonate (3.85 g, 22 mmol) was added dropwise in 10 mL tetrahydrofuran and stirring continued for 15 minutes to give a clear solution. Cyclohexanone (1.90 g, 19 mmol) was added in 5 mL tetrahydrofuran and the reaction mixture allowed to warm up to room temperature. The liquor was decanted and the residue washed three times with ether. The liquor and washings were combined, washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1 to give the required product as a colorless oil (1.5 g, 67%). chilled in ice under nitrogen to give a clear solution The liquor was decanted the residue washed three times with ether washed with dilute hydrochloric acid and water dried over magnesium sulphate filtered evaporated to dryness The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1

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

実験手順: The nitrile (compound 2, 0.78 g, 6.44 mmol), nitromethane (0.80 g, 13.11 mmol) and tetrabutyl ammonium fluoride (1.0 M in tetrahydrofuran, 10 mL, 10 mmol) were heated in 20 mL tetrahydrofuran to 70° C overnight. The reaction mixture was diluted with ethyl acetate and washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1 to give the required product as a yellow oil (0.83 g, 71%). washed with dilute hydrochloric acid and water dried over magnesium sulphate filtered evaporated to dryness The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1

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

実験手順: Sodium hydride (60% in oil, 0.80 g, 20 mmol) was suspended in 50 mL tetrahydrofuran and chilled in ice under nitrogen. Diethylcyanomethyl phosphonate (3.85 g, 22 mmol) was added dropwise in 10 mL tetrahydrofuran and stirring continued for 15 minutes to give a clear solution. Cyclohexanone (1.90 g, 19 mol) was added in 5 mL tetrahydrofuran and the reaction mixture allowed to warm up to room temperature. The liquor was decanted and the residue washed three times with ether. The liquor and washings were combined, washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1 to give the required product as a colorless oil (1.5 g. 67%). chilled in ice under nitrogen to give a clear solution The liquor was decanted the residue washed three times with ether washed with dilute hydrochloric acid and water dried over magnesium sulphate filtered evaporated to dryness The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1

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

実験手順: The nitrile (compound 2, 0.78 g, 6.44 mmol), nitromethane (0.80 g, 13.11 mmol) and tetrabutyl ammonium fluoride (1.0 M in tetrahydrofuran, 10 mL, 10 mmol) were heated in 20 mL tetrahydrofuran to 70° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1 to give the required product as a yellow oil (0.83 g, 71%). washed with dilute hydrochloric acid and water dried over magnesium sulphate filtered evaporated to dryness The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1

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

実験手順: Sodium hydride (60% in oil, 0.80 g, 20 mmol) was suspended in 50 mL tetrahydrofuran and chilled in ice under nitrogen. Diethylcyanomethyl phosphonate (3.85 g, 22 mmol) was added dropwise in 10 mL tetrahydrofuran and stirring continued for 15 minutes to give a clear solution. Cyclohexanone (1.90 g, 19 mmol) was added in 5 mL tetrahydrofuran and the reaction mixture allowed to warm up to room temperature. The liquor was decanted and the residue washed three times with ether. The liquor and washings were combined, washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1 to give the required product as a colorless oil (1.5 g, 67%). chilled in ice under nitrogen to give a clear solution The liquor was decanted the residue washed three times with ether washed with dilute hydrochloric acid and water dried over magnesium sulphate filtered evaporated to dryness The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1

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

実験手順: Sodium hydride (60% in oil, 0.80 g, 20 mmol) was suspended in 50 mL tetrahydrofuran and chilled in ice under nitrogen. Diethylcyanomethyl phosphonate (3.85 g, 22 mmol) was added dropwise in 10 mL tetrahydrofuran and stirring continued for 15 minutes to give a clear solution. Cyclohexanone (1.90 g, 19 mmol) was added in 5 mL tetrahydrofuran and the reaction mixture allowed to warm up to room temperature. The liquor was decanted and the residue washed three times with ether. The liquor and washings were combined, washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1 to give the required product as a colorless oil (1.5 g, 67%). chilled in ice under nitrogen to give a clear solution The liquor was decanted the residue washed three times with ether washed with dilute hydrochloric acid and water dried over magnesium sulphate filtered evaporated to dryness The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 4:1

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

実験手順: The nitrile (compound 2, 0.78 g, 6.44 mmol), nitromethane (0.80 g, 13.11 mmol) and tetrabutyl ammonium fluoride (1.0 M in tetrahydrofuran, 10 mL, 10 mmol) were heated in 20 mL tetrahydrofuran to 70° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with dilute hydrochloric acid and water, dried over magnesium sulphate, filtered, and evaporated to dryness. The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1 to give the required product as a yellow oil (0.83 g, 71%). washed with dilute hydrochloric acid and water dried over magnesium sulphate filtered evaporated to dryness The residue was purified by chromatography on silica eluting with heptane/ethyl acetate 3:1