3-butoxybenzaldehyde

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:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3-Hydroxybenzaldehyde (61 g) was added over 40 minutes to a suspension of sodium hydride (13.0 g) in dimethylformamide (700 cm3), the temperature of the reaction mixture being kept below 10° C. by means of a CO2 /oxitol bath. After stirring for 35 minutes, 1-bromobutane (73 g) was added dropwise over one hour and the mixture was then stirred at room temperature for 2.5 hours followed by heating at 85° C. for a further 2.5 hours. The resulting mixture was poured into ice water (1000 cm3) and was allowed to stand overnight before extracting with 40°-60° petrol/ether (3:1) (5×200 cm3). The combined organic layers were washed with 1M sodium hydroxide solution containing sodium chloride, dried over sodium sulphate, treated with activated charcoal, filtered and then evaporated down to give a golden brown mobile oil (79.7 g). the temperature of the reaction mixture being kept below 10° C. by means of a CO2 /oxitol bath the mixture was then stirred at room temperature for 2.5 hours to stand overnight before extracting with 40°-60° petrol/ether (3:1) (5×200 cm3) The combined organic layers were washed with 1M sodium hydroxide solution containing sodium chloride dried over sodium sulphate treated with activated charcoal filtered evaporated down

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-butoxy-benzaldehyde (4.23 g, 23.7 mmol) described in Manufacturing Example 65-1-1, nitromethane (2.55 mL, 47.7 mmol), ammonium acetate (2.74 g, 35.6 mmol) and acetic acid (40 mL) was stirred for 5 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (3.92 g, 75%). This mixture was cooled to room temperature concentrated under a reduced pressure diluted with ethyl acetate The organic layer was washed with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under a reduced pressure the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1)

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-butoxy-benzaldehyde (4.23 g, 23.7 mmol) described in Manufacturing Example 65-1-1, nitromethane (2.55 mL, 47.7 mmol), ammonium acetate (2.74 g, 35.6 mmol) and acetic acid (40 mL) was stirred for 5 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (3.92 g, 75%). This mixture was cooled to room temperature concentrated under a reduced pressure diluted with ethyl acetate The organic layer was washed with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under a reduced pressure the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1)

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

実験手順: 3-Hydroxybenzaldehyde (3 g, 24.6 mmol) and potassium carbonate (10.2 g, 73.8 mmol) were suspended in N,N-dimethylformamide (60 mL). 1-Bromobutane (3.17 mL, 29.5 mmol) was added to this suspension and stirred for 19 hours at room temperature. This mixture was partitioned into ethyl acetate and water. This organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (4.23 g). This mixture was partitioned into ethyl acetate and water This organic layer was separated washed with water dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under a reduced pressure

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-butoxy-benzaldehyde (4.23 g, 23.7 mmol) described in Manufacturing Example 65-1-1, nitromethane (2.55 mL, 47.7 mmol), ammonium acetate (2.74 g, 35.6 mmol) and acetic acid (40 mL) was stirred for 5 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (3.92 g, 75%). This mixture was cooled to room temperature concentrated under a reduced pressure diluted with ethyl acetate The organic layer was washed with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under a reduced pressure the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1)

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

実験手順: 3-Hydroxybenzaldehyde (3 g, 24.6 mmol) and potassium carbonate (10.2 g, 73.8 mmol) were suspended in N,N-dimethylformamide (60 mL). 1-Bromobutane (3.17 mL, 29.5 mmol) was added to this suspension and stirred for 19 hours at room temperature. This mixture was partitioned into ethyl acetate and water. This organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (4.23 g). This mixture was partitioned into ethyl acetate and water This organic layer was separated washed with water dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under a reduced pressure

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-butoxy-benzaldehyde (4.23 g, 23.7 mmol) described in Manufacturing Example 65-1-1, nitromethane (2.55 mL, 47.7 mmol), ammonium acetate (2.74 g, 35.6 mmol) and acetic acid (40 mL) was stirred for 5 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (3.92 g, 75%). This mixture was cooled to room temperature concentrated under a reduced pressure diluted with ethyl acetate The organic layer was washed with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under a reduced pressure the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1)

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

実験手順: 3-Hydroxybenzaldehyde (3 g, 24.6 mmol) and potassium carbonate (10.2 g, 73.8 mmol) were suspended in N,N-dimethylformamide (60 mL). 1-Bromobutane (3.17 mL, 29.5 mmol) was added to this suspension and stirred for 19 hours at room temperature. This mixture was partitioned into ethyl acetate and water. This organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (4.23 g). This mixture was partitioned into ethyl acetate and water This organic layer was separated washed with water dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under a reduced pressure

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-butoxy-benzaldehyde (4.23 g, 23.7 mmol) described in Manufacturing Example 65-1-1, nitromethane (2.55 mL, 47.7 mmol), ammonium acetate (2.74 g, 35.6 mmol) and acetic acid (40 mL) was stirred for 5 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1) to obtain the title compound (3.92 g, 75%). This mixture was cooled to room temperature concentrated under a reduced pressure diluted with ethyl acetate The organic layer was washed with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under a reduced pressure the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-1:1)

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

実験手順: 3-Hydroxybenzaldehyde (3 g, 24.6 mmol) and potassium carbonate (10.2 g, 73.8 mmol) were suspended in N,N-dimethylformamide (60 mL). 1-Bromobutane (3.17 mL, 29.5 mmol) was added to this suspension and stirred for 19 hours at room temperature. This mixture was partitioned into ethyl acetate and water. This organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (4.23 g). This mixture was partitioned into ethyl acetate and water This organic layer was separated washed with water dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under a reduced pressure