特戈拉赞杂质45

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: At about −20° C., 17.22 g (172.18 mmol) of chromium(VI) oxide were taken up in 1.2 l of acetone and 38 ml of water, and 19 ml of conc. sulfuric acid were slowly added to the mixture. The mixture was stirred for 10 min and then 8.10 g (43.05 mmol) of the compound from Example 168A in 400 ml of acetone were added dropwise over the course of 1 h. The mixture was stirred at 0° C. for 1.5 h. After addition of 90 ml of propan-2-ol, the reaction mixture was filtered through kieselguhr, the solvents were removed from the filtrate in vacuo, and the residue was taken up in 500 ml of diethyl ether. The solution was washed twice with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvents were removed in vacuo. 11.36 g of the title compound were obtained and were reacted further in the next stage without further purification. At about −20° C. The mixture was stirred at 0° C. for 1.5 h the reaction mixture was filtered through kieselguhr the solvents were removed from the filtrate in vacuo The solution was washed twice with saturated aqueous sodium chloride solution dried over sodium sulfate the solvents were removed in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: At about −20° C., 17.22 g (172.18 mmol) of chromium(VI) oxide were taken up in 1.2 l of acetone and 38 ml of water, and 19 ml of conc. sulfuric acid were slowly added to the mixture. The mixture was stirred for 10 min and then 8.10 g (43.05 mmol) of the compound from Example 168A in 400 ml of acetone were added dropwise over the course of 1 h. The mixture was stirred at 0° C. for 1.5 h. After addition of 90 ml of propan-2-ol, the reaction mixture was filtered through kieselguhr, the solvents were removed from the filtrate in vacuo, and the residue was taken up in 500 ml of diethyl ether. The solution was washed twice with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvents were removed in vacuo. 11.36 g of the title compound were obtained and were reacted further in the next stage without further purification. At about −20° C. The mixture was stirred at 0° C. for 1.5 h the reaction mixture was filtered through kieselguhr the solvents were removed from the filtrate in vacuo The solution was washed twice with saturated aqueous sodium chloride solution dried over sodium sulfate the solvents were removed in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2.77 g (69.18 mmol) of sodium hydride (60% in mineral oil) were dissolved in 80 ml of DMF. At 0° C., 7.50 g (57.65 mmol) of 3,5-difluorophenol in 15 ml of DMF were added dropwise and, after the gas evolution subsided, the mixture was stirred at RT for 30 min. The solution was cooled to 0° C., 5.45 g (57.65 mmol) of 3-chloro-1-propanol in 15 ml of DMF were added, and the mixture was then stirred at 60° C. for 2 h and at 75° C. for 16 h. The precipitated salts were filtered off, and DMF was removed in a rotary evaporator. The residue was taken up in water and extracted twice with diethyl ether. The combined organic phases were washed successively with water, 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the solvents were removed in vacuo. The crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient) to result in 8.15 g (75% of theory) of the title compound. The solution was cooled to 0° C. the mixture was then stirred at 60° C. for 2 h and at 75° C. for 16 h The precipitated salts were filtered off DMF was removed in a rotary evaporator extracted twice with diethyl ether The combined organic phases were washed successively with water, 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution dried over sodium sulfate filtered the solvents were removed in vacuo The crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient)

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: At about −20° C., 17.22 g (172.18 mmol) of chromium(VI) oxide were taken up in 1.2 l of acetone and 38 ml of water, and 19 ml of conc. sulfuric acid were slowly added to the mixture. The mixture was stirred for 10 min and then 8.10 g (43.05 mmol) of the compound from Example 168A in 400 ml of acetone were added dropwise over the course of 1 h. The mixture was stirred at 0° C. for 1.5 h. After addition of 90 ml of propan-2-ol, the reaction mixture was filtered through kieselguhr, the solvents were removed from the filtrate in vacuo, and the residue was taken up in 500 ml of diethyl ether. The solution was washed twice with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvents were removed in vacuo. 11.36 g of the title compound were obtained and were reacted further in the next stage without further purification. At about −20° C. The mixture was stirred at 0° C. for 1.5 h the reaction mixture was filtered through kieselguhr the solvents were removed from the filtrate in vacuo The solution was washed twice with saturated aqueous sodium chloride solution dried over sodium sulfate the solvents were removed in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2.77 g (69.18 mmol) of sodium hydride (60% in mineral oil) were dissolved in 80 ml of DMF. At 0° C., 7.50 g (57.65 mmol) of 3,5-difluorophenol in 15 ml of DMF were added dropwise and, after the gas evolution subsided, the mixture was stirred at RT for 30 min. The solution was cooled to 0° C., 5.45 g (57.65 mmol) of 3-chloro-1-propanol in 15 ml of DMF were added, and the mixture was then stirred at 60° C. for 2 h and at 75° C. for 16 h. The precipitated salts were filtered off, and DMF was removed in a rotary evaporator. The residue was taken up in water and extracted twice with diethyl ether. The combined organic phases were washed successively with water, 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered, and the solvents were removed in vacuo. The crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient) to result in 8.15 g (75% of theory) of the title compound. The solution was cooled to 0° C. the mixture was then stirred at 60° C. for 2 h and at 75° C. for 16 h The precipitated salts were filtered off DMF was removed in a rotary evaporator extracted twice with diethyl ether The combined organic phases were washed successively with water, 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution dried over sodium sulfate filtered the solvents were removed in vacuo The crude product was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate gradient)