methyl 3-oxoheptanoate

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:

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: 0.9 mol (150 ml) of methyl 3-oxoheptanoate and 2.7 mol (270 ml) butylamine, were stirred 5 h at 100° C. in the pressure vessel. Thereafter, excess butylamine was distilled off on a rotary evaporator, the crude product was taken up in water/ethanol, and adjusted with concentrated HCl to pH 3. The mixture was again evaporated to dryness, taken up again in ethyl acetate and filtered. The filtrate was washed with 1 M HCl and water. The organic phase was dried over Na2SO4 and after filtration evaporated in a rotary evaporator to dryness. The crude product was dissolved in 100 ml diethyl ether and crystallized at 5° C. The product was filtered off and dried. There were obtained 36.0 g of the title compound. Thereafter, excess butylamine was distilled off on a rotary evaporator The mixture was again evaporated to dryness filtered The filtrate was washed with 1 M HCl and water The organic phase was dried over Na2SO4 after filtration evaporated in a rotary evaporator to dryness The crude product was dissolved in 100 ml diethyl ether crystallized at 5° C The product was filtered off dried

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 0.632 mol (100 ml) methyl-3-oxoheptanoate (3-oxo-heptanoic acid methylester) and 227 ml 33% dimethylamine solution in ethanol (approx. 1.26 mol dimethylamine) was stirred for 4 hours at 110° C. in a pressure reactor. After cooling off, the solvents were distilled off on a rotavap, the raw product was taken up in 40 ml water, 30 ml 32% HCl and 40 ml ethanol and stirred for 24 hours at 100° C. The mixture was again concentrated to dryness by evaporation, taken up again in 300 ml acetic ester and filtrated, the solvents were then distilled off on the rotavap. 26 g of raw product was purified over 500 g silica gel 60 (mobile solvent: acetic ester:hexane 1:1, flow 50 ml/min, fraction size: 100 ml, product: fractions 20-35), the product was obtained as a mobile oil. 17.8 g of the title compound was obtained. After cooling off the solvents were distilled off on a rotavap The mixture was again concentrated to dryness by evaporation filtrated the solvents were then distilled off on the rotavap 26 g of raw product was purified over 500 g silica gel 60 (mobile solvent: acetic ester:hexane 1:1, flow 50 ml/min, fraction size: 100 ml, product: fractions 20-35) the product was obtained as a mobile oil

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 0.378 mol (60.2 ml) 3-oxo-heptanoic acid methylester, 400 ml 33% methylamine solution in ethanol and 40 ml water were stirred for 48 hours at 80° C. in a round-bottomed flask with a reflux condenser. After cooling off, the solvents were distilled off on a rotavap, the raw products were taken up in 200 ml water and 40 ml ethanol and set to about pH 3 with 40 ml 32% HCl. The reaction mixture was heated to 90° C. for 24 hours and then again concentrated to dryness in the rotavap. The raw product heated with 150 ml to reflux, filtrated hot and the filtrate was left to cool off. The product was filtrated off and dried in a vacuum drying cabinet at 50° C. 5.9 g of the title compound was obtained. After cooling off the solvents were distilled off on a rotavap again concentrated to dryness in the rotavap The raw product heated with 150 ml to reflux filtrated hot the filtrate was left to cool off The product was filtrated off dried in a vacuum drying cabinet at 50° C

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 0.4 mol (63.7 ml) 3-oxo-heptanoic acid methylester and 400 ml 7 N ammonia solution was stirred for three hours at 100° C. in a pressure reactor. After cooling off, the solvents were distilled off on a rotavap, the raw products were taken up in 200 ml water and 40 ml ethanol and set to about pH 3 with 40 ml 32% HCl. The reaction mixture was heated to 90° C. for 4 hours and then again concentrated to dryness in the rotavap, taken up in 600 ml dichloromethane and washed 3 times with 100 ml water. The organic phase was distilled off and the raw product recrystallized from 100 ml toluene. The product was filtrated off and dried in a vacuum drying cabinet at 50° C. 3.5 g of the title compound was obtained. After cooling off the solvents were distilled off on a rotavap again concentrated to dryness in the rotavap washed 3 times with 100 ml water The organic phase was distilled off the raw product recrystallized from 100 ml toluene The product was filtrated off dried in a vacuum drying cabinet at 50° C

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

実験手順: A mixture of 1.58 g (10 mmol) of methyl 3-oxoheptanoate, 1.85 g (10 mmol) of 4-bromobenzaldehyde, 0.04 ml of piperidine, 0.12 ml of acetic acid and 10 ml of toluene is heated to the refluxing temperature in a 25-ml round-bottomed flask equipped with a Dean and Stark apparatus. After two hours of heating, the theoretical amount of water is recovered and the toluene is evaporated off under vacuum. is heated to the refluxing temperature in a 25-ml round-bottomed flask equipped with a Dean and Stark apparatus After two hours of heating the theoretical amount of water is recovered the toluene is evaporated off under vacuum