2-(3-BROMOPHENOXY)ACETALDEHYDE DIETHYL ACETAL

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:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the acetal 6-2 in toluene (200 mL) was added polyphosphoric acid (20 g). The biphasic mixture was heated to 100° C. and stirred at this temperature for 4 h. The mixture was cooled to room temperature, poured onto ice, and extracted with Et2O (2×200 mL). The combined organic extracts were washed with saturated aq. NaHCO3 and brine. The solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (100% hexanes) to give the product 6-3 as a yellow oil. The mixture was cooled to room temperature poured onto ice extracted with Et2O (2×200 mL) The combined organic extracts were washed with saturated aq. NaHCO3 and brine The solution was dried over MgSO4 filtered concentrated The residue was purified by flash chromatography (100% hexanes)

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of NaH (2.77 g, 115.6 mmol) in DMF (100 mL) at 0° C. was added a solution of 3-bromophenol 6-1 in DMF (40 mL) over 40 min. After the addition was complete, the solution was stirred for an additional 30 min. The solution was then treated with neat bromoacetaldehyde diethyl acetal (17.36 g, 115.6 mmol). The solution was heated at 100° C. for 8 h, cooled to room temperature, and extracted with Et2O (3×200 mL). The combined organic extracts were washed with 10% aq. NaOH (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated to give 6-2 as a yellow oil. After the addition cooled to room temperature extracted with Et2O (3×200 mL) The combined organic extracts were washed with 10% aq. NaOH (100 mL) and brine (100 mL) dried over MgSO4 filtered concentrated

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the acetal 15-2 in toluene (200 mL) was added polyphosphoric acid (20 g). The biphasic mixture was heated to 100° C. and stirred at this temperature for 4 h. The mixture was cooled to room temperature, poured onto ice, and extracted with Et2O (2×200 mL). The combined organic extracts were washed with saturated aq NaHCO3 and brine. The solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (100% hexanes) to give the product 15-3 as a yellow oil. The mixture was cooled to room temperature poured onto ice extracted with Et2O (2×200 mL) The combined organic extracts were washed with saturated aq NaHCO3 and brine The solution was dried over MgSO4 filtered concentrated The residue was purified by flash chromatography (100% hexanes)

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of NaH (2.77 g, 115.6 mmol) in DMF (100 mL) at 0° C. was added a solution of 3-bromophenol 15-1 in DMF (40 mL) over 40 min. After the addition was complete, the solution was stirred for an additional 30 min. The solution was then treated with neat bromoacetaldehyde diethyl acetal (17.36 g, 115.6 mmol). The solution was heated at 100° C. for 8 h, cooled to room temperature, and extracted with Et2O (3×200 mL). The combined organic extracts were washed with 10% aq NaOH (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated to give 15-2 as a yellow oil. After the addition cooled to room temperature extracted with Et2O (3×200 mL) The combined organic extracts were washed with 10% aq NaOH (100 mL) and brine (100 mL) dried over MgSO4 filtered concentrated

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of NaH (2.77 g, 115.6 mmol) in DMF (100 mL) at 0° C. was added a solution of 3-bromophenol 3-1 in DMF (40 mL) over 40 min. After the addition was complete, the solution was stirred for an additional 30 min. The solution was then treated with neat bromoacetaldehyde diethyl acetal (17.36 g, 115.6 mmol). The solution was heated at 100° C. for 8 h, cooled to room temperature, and extracted with Et2O (3×200 mL). The combined organic extracts were washed with 10% aq. NaOH (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated to give 3-2 as a yellow oil. After the addition cooled to room temperature extracted with Et2O (3×200 mL) The combined organic extracts were washed with 10% aq. NaOH (100 mL) and brine (100 mL) dried over MgSO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the acetal 3-2 in toluene (200 mL) was added polyphosphoric acid (20 g). The biphasic mixture was heated to 100° C. and stirred at this temperature for 4 h. The mixture was cooled to room temperature, poured onto ice, and extracted with Et2O (2×200 mL). The combined organic extracts were washed with saturated aq. NaHCO3 and brine. The solution was dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (100% hexanes) to give the product 3-3 as a yellow oil. The mixture was cooled to room temperature poured onto ice extracted with Et2O (2×200 mL) The combined organic extracts were washed with saturated aq. NaHCO3 and brine The solution was dried over MgSO4 filtered concentrated The residue was purified by flash chromatography (100% hexanes)

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of NaH (2.77 g, 115.6 mmol) in DMF (100 mL) at 0° C. was added a solution of 3-bromophenol 3-1 in DMF (40 mL) over 40 min. After the addition was complete, the solution was stirred for an additional 30 min. The solution was then treated with neat bromoacetaldehyde diethyl acetal (17.36 g, 115.6 mmol). The solution was heated at 100° C. for 8 h, cooled to room temperature, and extracted with Et2O (3×200 mL). The combined organic extracts were washed with 10% aq. NaOH (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated to give 3-2 as a yellow oil. After the addition cooled to room temperature extracted with Et2O (3×200 mL) The combined organic extracts were washed with 10% aq. NaOH (100 mL) and brine (100 mL) dried over MgSO4 filtered concentrated