3,3-dimethoxypropanenitrile

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: A mixture of 2-amino-4'-methylbenzophenone (10 g), 3,3-dimethoxypropionitrile (10.9 g), p-toluenesulfonic acid. monohydrate (1.0 g) in toluene (120 ml) was heated under reflux for 4 hours. After addition of water, the reaction mixture was extracted with ethyl acetate and the extract was concentrated to dryness. The residue was purified by column chromatography on silica gel. Recrystallization from isopropyl ether afforded pale yellow prisms (5.67 g, 49%), m.p. 96°-97° C. was heated under reflux for 4 hours the reaction mixture was extracted with ethyl acetate the extract was concentrated to dryness The residue was purified by column chromatography on silica gel Recrystallization from isopropyl ether afforded pale yellow prisms (5.67 g, 49%), m.p. 96°-97° C.

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

実験手順: A mixture of 2-amino-4'-methylbenzophenone (10 g), 3,3-dimethoxypropionitrile (10.9 g), p-toluenesulfonic acid. monohydrate (1.0 g) in toluene (120 ml) was heated under reflux for 4 hours. After addition of water, the reaction mixture was extracted with ethyl acetate and the extract was concentrated to dryness. The residue was purified by column chromatography on silica gel. Recrystallization from isopropyl ether afforded pale yellow prisms (5.67 g, 49%), m.p. 96°-97° C. was heated under reflux for 4 hours the reaction mixture was extracted with ethyl acetate the extract was concentrated to dryness The residue was purified by column chromatography on silica gel Recrystallization from isopropyl ether afforded pale yellow prisms (5.67 g, 49%), m.p. 96°-97° C.

反応条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4.95 g of p-toluenesulfonic acid monohydrate was added to 30.0 g of 3,3-dimethoxypropionitrile, 67.63 g of benzyl alcohol and 100 ml of toluene, and the mixture was stirred at 110° C. for 8 hours. The reaction solution was returned to room temperature, and 5.26 g of triethylamine was added. After stirring for 5 minutes, the reaction solution was transferred to a separating funnel and washed with 200 ml of an aqueous 1 mass % potassium carbonate solution once and then with 200 ml of distilled solution three times. Toluene and the unreacted raw materials were removed by distillation under reduced pressure to obtain 60.6 g of 3,3-dibenzyloxypropionitrile. Thereto, 21.36 g of acetyl chloride was added, and the mixture was stirred at 45° C. for 6 hours. The reaction solution was returned to room temperature, and unreacted acetyl chloride was removed by distillation under reduced pressure. The reaction solution was analyzed by 1H-NMR, as a result, the concentration of 3-chloro-3-benzyloxypropionitrile in the reaction solution was 54.2 mass %. was returned to room temperature After stirring for 5 minutes the reaction solution was transferred to a separating funnel washed with 200 ml of an aqueous 1 mass % potassium carbonate solution once Toluene and the unreacted raw materials were removed by distillation under reduced pressure

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a three-necked flask, 61.6 g (0.55 mol) of potassium tert-butoxide were introduced into 250 ml of dimethoxyethane under N2 and the solution was cooled to 0° C. 4-Amino-1,1,1-trifluoro-3-buten-2-one, 69.5 g (0.5 mol), was added dropwise at this temperature in the course of 30 min and then 60.3 g (0.525 mol) of 3,3-dimethoxypropionitrile were added dropwise. The mixture was then stirred at 30° C. for 3-4 h. The reaction mixture was added to ice and acidified to pH 3-4 using HCl. The precipitate was filtered off and washed with water. The reaction mixture was added to ice The precipitate was filtered off washed with water

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

実験手順: To a suspension of NaH (60% dispersion in mineral oil, 2.52 g, 63.0 mmol) in diethylether (75 mL) was added 3,3-dimethoxypropanenitrile (6.17 mL, 55.0 mmol) followed by methyl formate (6.74 mL, 110 mmol). The solution was stirred for 3 days at RT. The resulting solid was collected by vacuum filtration and washed with ether to afford sodium (E)-2-cyano-3,3-dimethoxyprop-1-en-1-olate (4.2 g, 25.4 mmol). The resulting solid was collected by vacuum filtration washed with ether

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

実験手順: To a suspension of NaH (60% dispersion in mineral oil, 2.52 g, 63.0 mmol) in diethylether (75 mL) was added 3,3-dimethoxypropanenitrile (6.17 mL, 55.0 mmol) followed by methyl formate (6.74 mL, 110 mmol). The solution was stirred for 3 days at RT. The resulting solid was collected by vacuum filtration and washed with ether to afford sodium (E)-2-cyano-3,3-dimethoxyprop-1-en-1-olate (4.2 g, 25.4 mmol). The resulting solid was collected by vacuum filtration washed with ether

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

実験手順: Pyridine-3-carboxaldehyde (80.25 g, 0.75 mol) and 3,3-dimethoxypropionitrile (115.1 g, 1.0 mol) were mixed together and added to a solution of sodium methoxide (54.0 g, 1.0 mol) in methanol (400 mL) over a period of 15 minutes. The mixture was stirred at room temperature overnight. Most of the methanol was evaporated in vacuo and the residue was partitioned between ethyl acetate (500 mL) and water (450 mL). The organic layer was separated, washed with brine (400 mL), dried (MgSO4) and the solvent evaporated in vacuo. The residual oil was distilled in vacuo to give 80.3 g (52%) of the product as a colorless oil, bp 130-140° C. (2 mm Hg). Most of the methanol was evaporated in vacuo the residue was partitioned between ethyl acetate (500 mL) and water (450 mL) The organic layer was separated washed with brine (400 mL) dried (MgSO4) the solvent evaporated in vacuo The residual oil was distilled in vacuo

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

実験手順: Cyclohexanecarboxaldehyde (50.0 g, 0.45 mol) was added to a stirred mixture of 3,3-dimethoxypropionitrile (11.5, g, 1.0 mol) and sodium methoxide (54.0 g, 1.0 mol) in methanol over a period of 15 minutes. The mixture was then stirred overnight at room temperature.

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

実験手順: Cyclohexanecarboxaldehyde (50.0 g, 0.45 mol) was added to a stirred mixture of 3,3-dimethoxypropionitrile (11.5, g, 1.0 mol) and sodium methoxide (54.0 g, 1.0 mol) in methanol over a period of 15 minutes. The mixture was then stirred overnight at room temperature.