5-nitropentan-2-one

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: 80.0 g (0.61 mole) of 1-nitro-pentane-4-one are dissolved in 250 ml of anhydrous methanol, whereupon 31.5 ml (0.61 mole) of bromine are quickly added under cooling with ice. The reaction mixture is stirred for a further 2 hours at a rate that the internal temperature should not exceed 40° C. To the reaction mixture 250 ml of water are added, the reaction mixture is stirred at room temperature overnight. Next morning the solution is extracted three times with 300 ml of ether each, the etheral solution is washed with a 10 % sodium carbonate solution free of acid, whereupon it is washed three times with 200 ml of water each and 200 ml of a saturated sodium chloride solution, dried over calcium chloride and evaporated. The dry residue is subjected to chromatogaphy on a silica column and eluted with a 3:1 mixture of n-hexane and ethyl acetate. Thus 70.4 g of the desired compound are obtained in the form of a faint yellow liquid, yield 55%. Rf =0.30. IR(film) :2950, 1720, 640 cm-1. are quickly added under cooling with ice exceed 40° C the reaction mixture is stirred at room temperature overnight Next morning the solution is extracted three times with 300 ml of ether each, the etheral solution is washed with a 10 % sodium carbonate solution free of acid, whereupon it is washed three times with 200 ml of water each and 200 ml of a saturated sodium chloride solution dried over calcium chloride evaporated eluted with a 3:1 mixture of n-hexane and ethyl acetate

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark apparatus and under inert atmosphere (N2), crude 5-nitro-pentan-2-one (28.53 mmol) was dissolved in dry toluene (28 mL). Ethylene glycol (10.2 mL, 183.02 mmol) and p-TsOH (696 mg, 3.66 mmol) were added and the reaction mixture stirred at 120° C. for 5 h. The reaction mixture was then cooled down to rt and sat. aq. NaHCO3 was added. The layers were separated and the org. layer washed with brine (2×), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 4:1) to give the title compound as a pale brown oil. TLC:rf (4:1 hept-EA)=0.21. In a flame dried round-bottomed flask equipped with a magnetic stir bar The reaction mixture was then cooled down to rt The layers were separated layer washed with brine (2×) dried over Na2SO4 filtered concentrated under reduced pressure The crude residue was purified by FC (hept-EA, 4:1)

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark apparatus and under inert atmosphere (N2), crude 5-nitro-pentan-2-one (28.53 mmol) was dissolved in dry toluene (28 mL). Ethylene glycol (10.2 mL, 183.02 mmol) and p-TsOH (696 mg, 3.66 mmol) were added and the reaction mixture stirred at 120° C. for 5 h. The reaction mixture was then cooled down to rt and sat. aq. NaHCO3 was added. The layers were separated and the org. layer washed with brine (2×), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 4:1) to give the title compound as a pale brown oil. TLC:rf (4:1 hept-EA)=0.21. In a flame dried round-bottomed flask equipped with a magnetic stir bar The reaction mixture was then cooled down to rt The layers were separated layer washed with brine (2×) dried over Na2SO4 filtered concentrated under reduced pressure The crude residue was purified by FC (hept-EA, 4:1)

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

実験手順: In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of methyl vinyl ketone (2.32 mL, 28.53 mmol) in nitromethane (29.6 mL) was added activated KF/Al2O3 (323 mg, prepared by mixing KF and basic Al2O3 in water followed by concentrating and drying) at 0° C. The reaction mixture was then allowed to warm up to rt and stirred at this temperature for 18 h. The mixture was filtered through neutral Al2O3 and washed with CH2Cl2. The filtrated was concentrated under reduced pressure to give the title compound as a colorless oil. was added at 0° C The mixture was filtered through neutral Al2O3 washed with CH2Cl2 The filtrated was concentrated under reduced pressure

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

実験手順: Methyl vinyl ketone (4.17 ml, 0.05 moles), nitromethane (24.4 ml, 0.45 moles) and THF (250 ml) were mixed and stirred together under nitrogen. Potassium fluoride on alumina (10 g) was added and the mixture stirred for 2 hours at ambient temperature. The reaction was filtered and the filtrate was evaporated to give crude 5-nitro-2-pentanone as a pale yellow oil (6.11 g, 93%). the mixture stirred for 2 hours at ambient temperature The reaction was filtered the filtrate was evaporated

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: 80.0 g (0.61 mole) of 1-nitro-pentane-4-one are dissolved in 250 ml of anhydrous methanol, whereupon 31.5 ml (0.61 mole) of bromine are quickly added under cooling with ice. The reaction mixture is stirred for a further 2 hours at a rate that the internal temperature should not exceed 40° C. To the reaction mixture 250 ml of water are added, the reaction mixture is stirred at room temperature overnight. Next morning the solution is extracted three times with 300 ml of ether each, the etheral solution is washed with a 10 % sodium carbonate solution free of acid, whereupon it is washed three times with 200 ml of water each and 200 ml of a saturated sodium chloride solution, dried over calcium chloride and evaporated. The dry residue is subjected to chromatogaphy on a silica column and eluted with a 3:1 mixture of n-hexane and ethyl acetate. Thus 70.4 g of the desired compound are obtained in the form of a faint yellow liquid, yield 55%. Rf =0.30. IR(film) :2950, 1720, 640 cm-1. are quickly added under cooling with ice exceed 40° C the reaction mixture is stirred at room temperature overnight Next morning the solution is extracted three times with 300 ml of ether each, the etheral solution is washed with a 10 % sodium carbonate solution free of acid, whereupon it is washed three times with 200 ml of water each and 200 ml of a saturated sodium chloride solution dried over calcium chloride evaporated eluted with a 3:1 mixture of n-hexane and ethyl acetate

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a flame dried round-bottomed flask equipped with a magnetic stir bar and a Dean-Stark apparatus and under inert atmosphere (N2), crude 5-nitro-pentan-2-one (28.53 mmol) was dissolved in dry toluene (28 mL). Ethylene glycol (10.2 mL, 183.02 mmol) and p-TsOH (696 mg, 3.66 mmol) were added and the reaction mixture stirred at 120° C. for 5 h. The reaction mixture was then cooled down to rt and sat. aq. NaHCO3 was added. The layers were separated and the org. layer washed with brine (2×), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 4:1) to give the title compound as a pale brown oil. TLC:rf (4:1 hept-EA)=0.21. In a flame dried round-bottomed flask equipped with a magnetic stir bar The reaction mixture was then cooled down to rt The layers were separated layer washed with brine (2×) dried over Na2SO4 filtered concentrated under reduced pressure The crude residue was purified by FC (hept-EA, 4:1)

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

実験手順: In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of methyl vinyl ketone (2.32 mL, 28.53 mmol) in nitromethane (29.6 mL) was added activated KF/Al2O3 (323 mg, prepared by mixing KF and basic Al2O3 in water followed by concentrating and drying) at 0° C. The reaction mixture was then allowed to warm up to rt and stirred at this temperature for 18 h. The mixture was filtered through neutral Al2O3 and washed with CH2Cl2. The filtrated was concentrated under reduced pressure to give the title compound as a colorless oil. was added at 0° C The mixture was filtered through neutral Al2O3 washed with CH2Cl2 The filtrated was concentrated under reduced pressure