4-methyl-1-phenylpentan-3-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:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-phenylpropionic acid (13.0 g, 86.6 mmol), 2,3-dihydrofuran (6.67 g, 95.2 mmol) and dichloromethane (90 ml) was cooled to −60° C., followed by adding thereto a solution of methanesulfonic acid (0.012 g, 0.13 mmol) in dichloromethane (1 ml). The reaction mixture was heated to −5° C. and stirred at this temperature for 4 hours. The reaction mixture was re-cooled to −60° C., followed by adding dropwise thereto isopropylmagnesium chloride (a 2M tetrahydrofuran solution; 48 ml, 95.2 mmol), and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into a cooled aqueous phosphoric acid solution and extracted with chloroform. The extract solution was washed successively with water, a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography to obtain 5.97 g of 4-methyl-1-phenylpentan-3-one. by adding The reaction mixture was heated to −5° C. The reaction mixture was re-cooled to −60° C. by adding dropwise 48 ml, 95.2 mmol), and the resulting mixture was stirred at room temperature for 16 hours extracted with chloroform The extract solution was washed successively with water a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the resulting residue was purified by a silica gel column chromatography

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

実験手順: Lithium chloride (27 mmol) and copper (I) chloride (13.46 mmol) are weighed into a flame dried 250 mL round-bottomed flask fitted with low temperature thermometer. Dry THF (50 mL) is added and the mixture stirred at RT for 1 h to give a cloudy yellow-green solution. This is cooled to −55° C. and isopropylmagnesium chloride (6.75 mL of a 2 M solution in THF, 13.5 mmol) is added. After 15 min hydrocinnamoyl chloride (13.46 mmol) is added quickly at −60° C. and the mixture allowed to warm slowly to RT overnight. The mixture is quenched with water (100 mL) and 35% ammonium hydroxide (20 mL) is added. The mixture is stirred at RT for 1 h and then extracted with diethyl ether (3×50 mL). The combined ether extracts are washed with saturated brine (50 mL), dried (MgSO4), filtered and evaporated under reduced pressure to give 4-methyl-1-phenyl-pentan-3-one. dried 250 mL round-bottomed flask fitted with low temperature Dry THF (50 mL) is added to give a cloudy yellow-green solution This is cooled to −55° C. to warm slowly to RT overnight The mixture is quenched with water (100 mL) and 35% ammonium hydroxide (20 mL) is added The mixture is stirred at RT for 1 h extracted with diethyl ether (3×50 mL) The combined ether extracts are washed with saturated brine (50 mL) dried (MgSO4) filtered evaporated under reduced pressure

反応条件: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-phenylpropionic acid (13.0 g, 86.6 mmol), 2,3-dihydrofuran (6.67 g, 95.2 mmol) and dichloromethane (90 ml) was cooled to −60° C., followed by adding thereto a solution of methanesulfonic acid (0.012 g, 0.13 mmol) in dichloromethane (1 ml). The reaction mixture was heated to −5° C. and stirred at this temperature for 4 hours. The reaction mixture was re-cooled to −60° C., followed by adding dropwise thereto isopropylmagnesium chloride (a 2M tetrahydrofuran solution; 48 ml, 95.2 mmol), and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into a cooled aqueous phosphoric acid solution and extracted with chloroform. The extract solution was washed successively with water, a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography to obtain 5.97 g of 4-methyl-1-phenylpentan-3-one. by adding The reaction mixture was heated to −5° C. The reaction mixture was re-cooled to −60° C. by adding dropwise 48 ml, 95.2 mmol), and the resulting mixture was stirred at room temperature for 16 hours extracted with chloroform The extract solution was washed successively with water a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the resulting residue was purified by a silica gel column chromatography

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

実験手順: Lithium chloride (27 mmol) and copper (I) chloride (13.46 mmol) are weighed into a flame dried 250 mL round-bottomed flask fitted with low temperature thermometer. Dry THF (50 mL) is added and the mixture stirred at RT for 1 h to give a cloudy yellow-green solution. This is cooled to −55° C. and isopropylmagnesium chloride (6.75 mL of a 2 M solution in THF, 13.5 mmol) is added. After 15 min hydrocinnamoyl chloride (13.46 mmol) is added quickly at −60° C. and the mixture allowed to warm slowly to RT overnight. The mixture is quenched with water (100 mL) and 35% ammonium hydroxide (20 mL) is added. The mixture is stirred at RT for 1 h and then extracted with diethyl ether (3×50 mL). The combined ether extracts are washed with saturated brine (50 mL), dried (MgSO4), filtered and evaporated under reduced pressure to give 4-methyl-1-phenyl-pentan-3-one. dried 250 mL round-bottomed flask fitted with low temperature Dry THF (50 mL) is added to give a cloudy yellow-green solution This is cooled to −55° C. to warm slowly to RT overnight The mixture is quenched with water (100 mL) and 35% ammonium hydroxide (20 mL) is added The mixture is stirred at RT for 1 h extracted with diethyl ether (3×50 mL) The combined ether extracts are washed with saturated brine (50 mL) dried (MgSO4) filtered evaporated under reduced pressure