4-(dimethylamino)-3-phenylbut-3-en-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:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-dimethylamino-3-phenyl-3-butene-2-one (14.1 grams) and cyanoacetamide (5.9 grams) in 100 ml methanol was added to sodium methoxide (7.9 grams) in 100 ml methanol. The mixture was refluxed for 18 hours and then the crude reaction was stripped and the residue dissolved in a small amount of hot water. Acidification to pH 6-7 gave a gum-like solid which was collected by filtration. Further acidification to a lower pH gave only an oil. Trituration of the gum with ethyl acetate and chilling resulted in an off-white solid which was identified by NMR as the desired product, yield 2.8 grams, m.p. 280°-290° C. The mixture was refluxed for 18 hours the crude reaction Acidification to pH 6-7 gave a gum-like solid which was collected by filtration Further acidification to a lower pH gave only an oil resulted in an off-white solid which

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

実験手順: A mixture of phenylacetone (13.4 grams) and dimethylformamide dimethylacetal (13.0 grams) was heated at 90°-95° C. on a steam bath for about 21/2 hours. A crude oil was produced which was then chromatographed on 600 ml of silica gel using ethyl acetate as an eluent. The final product, whose structure was confirmed by NMR, was a yellow oil which crystallized upon standing, yield 15.5 grams. was heated at 90°-95° C. on a steam bath for about 21/2 hours A crude oil was produced which was then chromatographed on 600 ml of silica gel crystallized

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

実験手順: A mixture of 4-dimethylamino-3-phenyl-3-butene-2-one (14.1 grams) and cyanoacetamide (5.9 grams) in 100 ml methanol was added to sodium methoxide (7.9 grams) in 100 ml methanol. The mixture was refluxed for 18 hours and then the crude reaction was stripped and the residue dissolved in a small amount of hot water. Acidification to pH 6-7 gave a gum-like solid which was collected by filtration. Further acidification to a lower pH gave only an oil. Trituration of the gum with ethyl acetate and chilling resulted in an off-white solid which was identified by NMR as the desired product, yield 2.8 grams, m.p. 280°-290° C. The mixture was refluxed for 18 hours the crude reaction Acidification to pH 6-7 gave a gum-like solid which was collected by filtration Further acidification to a lower pH gave only an oil resulted in an off-white solid which

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

実験手順: A mixture of phenylacetone (13.4 grams) and dimethylformamide dimethylacetal (13.0 grams) was heated at 90°-95° C. on a steam bath for about 21/2 hours. A crude oil was produced which was then chromatographed on 600 ml of silica gel using ethyl acetate as an eluent. The final product, whose structure was confirmed by NMR, was a yellow oil which crystallized upon standing, yield 15.5 grams. was heated at 90°-95° C. on a steam bath for about 21/2 hours A crude oil was produced which was then chromatographed on 600 ml of silica gel crystallized

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

実験手順: A suspension of sodium ethoxide was prepared by addition of ethanol (1.6 ml) to a stirred suspension of sodium hydride (1.3 g 50% dispersion, washed with petroleum spirit 40°-60° C.) in ether (50 ml) under nitrogen. A solution of 4-dimethylamino-3-phenyl-3-buten-2-one (4.8 g) and diethyl oxalate (5.2 ml) in ether (50 ml) was added to the stirred sodium ethoxide suspension at 5° to 10° C. and the resulting clear solution was stirred for 2 hours at room temperature, then cooled and treated with glacial acetic acid (2.5 ml) and water (50 ml). Ethyl acetate was added to dissolve the solid which formed and the solvent layer was washed with water, dried, and evaporated. The solid residue was recrystallised from ethyl acetate-petroleum spirit (60°-80° C.) to give ethyl 6-dimethylamino-2,4-dioxo-5-phenyl-5-hexenoate (mp 110° C.). cooled to dissolve the solid which formed the solvent layer was washed with water dried evaporated The solid residue was recrystallised from ethyl acetate-petroleum spirit (60°-80° C.)

反応条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-dimethylamino-3-phenyl-3-buten-2-one (30.3 g) and diethyl oxalate (43.5 ml) in ethanol (75 ml) was added to a stirred solution of sodium ethoxide prepared by dissolving sodium (5.5 g) in ethanol (150 ml). The stirred mixture was heated under reflux for 1 hour, cooled to 20°-25° C. and acidified by addition of 5 N hydrochloric acid (150 ml). The mixture was stirred for a further hour, then cooled to 5° C., and diluted with water (300 ml). The solid title product was recrystallised from ethanol-water (mp 110°-112° C.). prepared The stirred mixture was heated under reflux for 1 hour cooled to 20°-25° C. The solid title product was recrystallised from ethanol-water (mp 110°-112° C.)

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

実験手順: A stirred mixture of benzyl methyl ketone (26.8 ml) and dimethylformamide dimethyl acetal (30.0 ml) was heated in a distillation apparatus on an oil bath at 95°-100° C. for 11/2 hours. Methanol slowly distilled off. The residual volatiles were removed under vacuum and the resulting oil was crystallised from ether-petroleum spirit (40°-60° C.) to yield the title compound (mp 66° C.). was heated in a distillation apparatus on an oil bath at 95°-100° C. for 11/2 hours Methanol slowly distilled off The residual volatiles were removed under vacuum the resulting oil was crystallised from ether-petroleum spirit (40°-60° C.)