4-oxo-4-phenylbutanenitrile

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 320 ml of absolute dimethylformamide, 42.5 g (0.4 mol) of freshly distilled benzaldehyde and 9.8 g (0.2 mol) of sodium cyanide are introduced into a 500 ml 4-necked flask equipped with dropping funnel, stirrer, KOH drying tube and internal thermometer. A week exothermic reaction takes place after the addition of sodium cyanide to the reaction mixture and the temperature rises from 30° to 34° C. The reaction mixture is stirred for 15 minutes at a reaction temperature of 30° C and a solution of 15.9 g (0.3 mol) of freshly distilled acrylonitrile and 80 ml of absolute dimethylformamide is introduced dropwise into the reaction mixture in the course of one hour at the same temperature. Stirring is then continued for 1/4 hours at the same temperature. The reaction mixture, which is now very creamy, is poured on to 800 ml of water and vigorously shaken. The aqueous solution is extracted twice with 200 ml of chloroform and twice with 100 ml of chloroform. The combined chloroform solutions are vigorously washed with water and dried over MgSO4 and the chloroform is distilled off. Inoculating crystals are added to the residue. β-Benzoyl-propionitrile then crystallises at once. It is suction filtered and washed with ethanol. 26.6 g of β-benzoylpropionitrile are obtained. M.p.: 69° C. equipped A week exothermic reaction rises from 30° to 34° C Stirring is then continued for 1/4 hours at the same temperature vigorously shaken The aqueous solution is extracted twice with 200 ml of chloroform and twice with 100 ml of chloroform The combined chloroform solutions are vigorously washed with water dried over MgSO4 the chloroform is distilled off Inoculating crystals are added to the residue β-Benzoyl-propionitrile then crystallises at once filtered washed with ethanol

反応条件: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 320 ml of absolute dimethylformamide, 42.5 g (0.4 mol) of freshly distilled benzaldehyde and 9.8 g (0.2 mol) of sodium cyanide are introduced into a 500 ml 4-necked flask equipped with dropping funnel, stirrer, KOH drying tube and internal thermometer. A week exothermic reaction takes place after the addition of sodium cyanide to the reaction mixture and the temperature rises from 30° to 34° C. The reaction mixture is stirred for 15 minutes at a reaction temperature of 30° C and a solution of 15.9 g (0.3 mol) of freshly distilled acrylonitrile and 80 ml of absolute dimethylformamide is introduced dropwise into the reaction mixture in the course of one hour at the same temperature. Stirring is then continued for 1/4 hours at the same temperature. The reaction mixture, which is now very creamy, is poured on to 800 ml of water and vigorously shaken. The aqueous solution is extracted twice with 200 ml of chloroform and twice with 100 ml of chloroform. The combined chloroform solutions are vigorously washed with water and dried over MgSO4 and the chloroform is distilled off. Inoculating crystals are added to the residue. β-Benzoyl-propionitrile then crystallises at once. It is suction filtered and washed with ethanol. 26.6 g of β-benzoylpropionitrile are obtained. M.p.: 69° C. equipped A week exothermic reaction rises from 30° to 34° C Stirring is then continued for 1/4 hours at the same temperature vigorously shaken The aqueous solution is extracted twice with 200 ml of chloroform and twice with 100 ml of chloroform The combined chloroform solutions are vigorously washed with water dried over MgSO4 the chloroform is distilled off Inoculating crystals are added to the residue β-Benzoyl-propionitrile then crystallises at once filtered washed with ethanol

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a solution of 4-oxo-4-phenylbutanenitrile (0.076 g, 0.48 mmol) in ethanol (5 mL) was added 2,5-difluorobenzothiohydrazide (0.09 g, 0.48 mmol). After stirring at 90° C. for 16 hours, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed (20% ethyl acetate in hexanes) to provide the product (0.087 g, 55% yield). the reaction mixture was concentrated under reduced pressure The residue was dissolved in ethyl acetate washed with water and brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was chromatographed (20% ethyl acetate in hexanes)

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

実験手順: To a solution of 3-chloro-1-phenylpropan-1-one (5.0 g, 29.7 mmol) in hot ethanol (7 mL) was added potassium acetate (2.91 g, 29.77 mmol). After cooling to room temperature, the precipitated salt was removed via filtration. To the filtrate in a septum-sealed flask under a nitrogen bubbler was slowly added sodium cyanide (2.91 g, 59.3 mmol) as a solution in water (10 mL). After stirring at room temperature for 24 hours, ethanol (30 mL) was added, and the mixture was cooled in an ice bath. The precipitate was filtered and rinsed with ethanol to provide the product (3.42 g, 73%) as fluffy white solid. the precipitated salt was removed via filtration To the filtrate in a septum-sealed flask under a nitrogen bubbler was slowly added the mixture was cooled in an ice bath The precipitate was filtered rinsed with ethanol

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Based on Kulkarni, N. R. Ayyangar, Tetrahedron, 1994, 50, 1243–1260. ]: A mixture of 3-bromopropiophenone (10.65 g, 50 mmol), CuCN (5.82 g, 65 mmol) in DMF (35 mL) was heated under reflux for 6 h. After cooling the mixture to ambient temperature FeCl3 (5 g) in H2O (30 mL)/HCl conc (10 mL) was added and heated to 80° C. for another 20 min. After cooling to room temperature and extraction with ether further purification occurred by destination under reduced pressure (bp.: 140° C., 10 torr). The ketone could be obtained as slightly yellow, low melting (42° C.) solid. was heated under reflux for 6 h was added After cooling to room temperature extraction with ether further purification

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

実験手順: In this Step, a phenacyl acetonitrile compound of formula (17) is prepared by alkylating the cyano compound of formula (16) with a phenacyl halide compound of formula (7). This reaction is essentially the same as and may be carried out in the same manner as and using the same reagents and reaction conditions as Step B3 of Method B. the same reagents and reaction conditions as Step B3 of Method B

反応条件: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 320 ml of absolute dimethylformamide, 42.5 g (0.4 mol) of freshly distilled benzaldehyde and 9.8 g (0.2 mol) of sodium cyanide are introduced into a 500 ml 4-necked flask equipped with dropping funnel, stirrer, KOH drying tube and internal thermometer. A week exothermic reaction takes place after the addition of sodium cyanide to the reaction mixture and the temperature rises from 30° to 34° C. The reaction mixture is stirred for 15 minutes at a reaction temperature of 30° C and a solution of 15.9 g (0.3 mol) of freshly distilled acrylonitrile and 80 ml of absolute dimethylformamide is introduced dropwise into the reaction mixture in the course of one hour at the same temperature. Stirring is then continued for 1/4 hours at the same temperature. The reaction mixture, which is now very creamy, is poured on to 800 ml of water and vigorously shaken. The aqueous solution is extracted twice with 200 ml of chloroform and twice with 100 ml of chloroform. The combined chloroform solutions are vigorously washed with water and dried over MgSO4 and the chloroform is distilled off. Inoculating crystals are added to the residue. β-Benzoyl-propionitrile then crystallises at once. It is suction filtered and washed with ethanol. 26.6 g of β-benzoylpropionitrile are obtained. M.p.: 69° C. equipped A week exothermic reaction rises from 30° to 34° C Stirring is then continued for 1/4 hours at the same temperature vigorously shaken The aqueous solution is extracted twice with 200 ml of chloroform and twice with 100 ml of chloroform The combined chloroform solutions are vigorously washed with water dried over MgSO4 the chloroform is distilled off Inoculating crystals are added to the residue β-Benzoyl-propionitrile then crystallises at once filtered washed with ethanol

反応条件: temp:0.00; pressure:0.00; stir: