2,2,8,8-tetramethylnona-3,6-diyn-5-ol

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 Jones' reagent (2.2 L) was added dropwise to a solution of 2,2,8,8-tetramethylnona-3,6-diyn-5-ol (500 g, 2.6 mol, prepared in Part A above) in acetone (1.5 L), and the rapid, exothermic reaction which followed was monitored by thin layer chromatography for disappearance of starting material. When this had been observed, the two-phase mixture was poured with agitation into ice/water, and the resultant precipitate was filtered and washed with water until a colorless filtrate was obtained. Air drying afforded 2,2,8,8-tetramethylnona-3,6-diyn-5-one (471 g, 94% yield) as pale yellow crystals which melted at 65-66° C. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy. the rapid, exothermic reaction which the resultant precipitate was filtered washed with water until a colorless filtrate was obtained Air drying

反応条件: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The 2,2,8,8-tetramethylnona-3,6-diyn-5-ol prepared in Part A (7.0 g, 36 mmole) was dissolved in 150 mL of benzene, cooled to 5-10° C. and nickel peroxide (18.15 g, 200 mmole) was added over a period of 20 minutes. After the addition had been completed, the reaction mixture was stirred at room temperature for 30 minutes, then filtered, and the nickel peroxide left on the filter was washed well with benzene and then with dichloromethane. The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene to give 2,2,8,8-tetramethylnona-3,6-diyn-5-one as pale yellow crystals (4.2 g). The structure of this product was confirmed by fast atom bombardment (FAB) mass spectroscopy. After the addition filtered the nickel peroxide left on the filter was washed well with benzene The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene

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

実験手順: The Jones' reagent (2.2 L) was added dropwise to a solution of 2,2,8,8-tetramethylnona-3,6-diyn-5-ol (500 g, 2.6 mol, prepared in Part A above) in acetone (1.5 L), and the rapid, exothermic reaction which followed was minitored by thin layer chromatography for disappearance of starting material. When this had been observed, the two-phase mixture was poured with agitation into ice/water, and the resultant precipitate was filtered and washed with water until a colorless filtrate was obtained. Air drying afforded 2,2,8,8-tetramethylnona-3,6-diyn-5-one (471 g, 94% yield) as pale yellow crystals which melted at 65-66° C. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy. the rapid, exothermic reaction which the resultant precipitate was filtered washed with water until a colorless filtrate was obtained Air drying

反応条件: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The 2,2,8,8-tetramethylnona-3,6-diyn-5-ol prepared in Part A (7.0 g, 36 mmole) was dissolved in 150 mL of benzene, cooled to 5-10° C. and nickel peroxide (18.15 g, 200 mmole) was added over a period of 20 minutes. After the addition had been completed, the reaction mixture was stirred at room temperature for 30 minutes, then filtered, and the nickel peroxide left on the filter was washed well with benzene and then with dichloromethane. The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene to give 2,2,8,8-tetramethylnona-3,6-diyn-5-one as pale yellow crystals (4.2 g). The structure of this product was confirmed by fast atom bombardment (FAB) mass spectroscopy. After the addition filtered the nickel peroxide left on the filter was washed well with benzene The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene

反応条件: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The 2,2,8,8-tetramethylnona-3,6-diyn-5-ol prepared in Part A (7.0 g, 36 mmole) was dissolved in 150 mL of benzene, cooled to 5-10° C. and nickel peroxide (18.15 g, 200 mmole) was added over a period of 20 minutes. After the addition had been completed, the reaction mixture was stirred at room temperature for 30 minutes, then filtered, and the nickel peroxide left on the filter was washed well with benzene and then with dichloromethane. The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene to give 2,2,8,8-tetramethylnona-3,6-diyn-5-one as pale yellow crystals (4.2 g). The structure of this product was confirmed by fast atom bombardment (FAB) mass spectroscopy. After the addition filtered the nickel peroxide left on the filter was washed well with benzene The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene

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

実験手順: The Jones' reagent (2.2 L) was added dropwise to a solution of 2,2,8,8-tetramethylnona-3,6-diyn-5-ol (500 g, 2.6 mol, prepared in Part A above) in acetone (1.5 L), and the rapid, exothermic reaction which followed was monitored by thin layer chromatography for disappearance of starting material. When this had been observed, the two-phase mixture was poured with agitation into ice/water, and the resultant precipitate was filtered and washed with water until a colorless filtrate was obtained. Air drying afforded 2,2,8,8-tetramethylnona-3,6-diyn-5-one (471 g, 94% yield) as pale yellow crystals which melted at 65°-66° C. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy. the rapid, exothermic reaction which the resultant precipitate was filtered washed with water until a colorless filtrate was obtained Air drying

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

実験手順: The 2,2,8,8-tetramethyl-nona-3,6-diyn-5-ol prepared in Part A (7.0 g, 36 mmole) was dissolved in 150 mL of benzene, cooled to 5°-10° C. and nickel peroxide (18.15 g, 465 mmole) was added over a period of 20 minutes. After the addition had been completed, the reaction mixture was stirred at room temperature for 30 minutes, then filtered, and the nickel peroxide left on the filter was washed well with benzene and then with dichloromethane. The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene to give 2,2,8,8-tetramethyl-nona-3,6-diyn-5-one as pale yellow crystals (4.2 g). The structure of this product was confirmed by FAB mass spectroscopy. cooled to 5°-10° C. After the addition filtered the nickel peroxide left on the filter was washed well with benzene The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene

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

実験手順: The 2,2,8,8-tetramethyl-nona-3,6-diyn-5-ol prepared in Part A (7.0 g, 36 mmole) was dissolved in 150 mL of benzene, cooled to 5°-10° C. and nickel peroxide (18.15 g, 465 mmole) was added over a period of 20 minutes. After the addition had been completed, the reaction mixture was stirred at room temperature for 30 minutes, then filtered, and the nickel peroxide left on the filter was washed well with benzene and then with dichloromethane. The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene to give 2,2,8,8-tetramethyl-nona-3,6-diyn-5-one as pale yellow crystals (4.2 g). The structure of this product was confirmed by FAB mass spectroscopy. cooled to 5°-10° C. After the addition filtered the nickel peroxide left on the filter was washed well with benzene The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene

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 Jones' reagent (2.2 L) was added dropwise to a solution of 2,2,8,8-tetramethylnona-3,6-diyn-5-ol (500 g, 2.6 mol, prepared in Part A above) in acetone (1.5 L), and the rapid, exothermic reaction which followed was monitored by thin layer chromatography for disappearance of starting material. When this had been observed, the two-phase mixture was poured with agitation into ice/water, and the resultant precipitate was filtered and washed with water until a colorless filtrate was obtained. Air drying afforded 2,2,8,8-tetramethylnona-3,6-diyn-5-one (471 g, 94% yield) as pale yellow crystals which melted at 65-66° C. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy. the rapid, exothermic reaction which the resultant precipitate was filtered washed with water until a colorless filtrate was obtained Air drying

反応条件: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The 2,2,8,8-tetramethylnona-3,6-diyn-5-ol prepared in Part A (7.0 g, 36 mmole) was dissolved in 150 mL of benzene, cooled to 5-10° C. and nickel peroxide (18.15 g, 200 mmole) was added over a period of 20 minutes. After the addition had been completed, the reaction mixture was stirred at room temperature for 30 minutes, then filtered, and the nickel peroxide left on the filter was washed well with benzene and then with dichloromethane. The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene to give 2,2,8,8-tetramethylnona-3,6-diyn-5-one as pale yellow crystals (4.2 g). The structure of this product was confirmed by fast atom bombardment (FAB) mass spectroscopy. After the addition filtered the nickel peroxide left on the filter was washed well with benzene The filtrate was evaporated to give a yellow solid, which was recrystallized from benzene