烯丙基苯乙基醚

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: To a cooled (0° C.) solution of 2-allyloxyethylbenzene (5. g; 30.8 mmol) dissolved in THF (75 ml) is slowly added a 0.5M THF solution of 9-BBN [9-borabicyclo[3.3.1]nonane] (68 ml; 34 mmol) and the reaction mixture warmed to room temperature and stirred for 4 hours. The reaction mixture is then cooled to 0° C. and 5 ml H2O is added followed by slow addition of 6N NaOH (30 ml; 7.2 g/30 ml). After stirring for 5 minutes, 30% H2O2 (20 ml)is added over 15 min. The reaction mixture warms significantly but is kept from refluxing. After addition is complete, it is stirred for 15 minutes allowing the mixture to come to room temperature. It is then diluted with Et2O, washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine, dried (MgSO4) and concentrated to dryness. The residue is purified by column chromatography using Et2O to obtain 3-(2-phenylethoxy)-1-propanol which is used directly in Step C. The reaction mixture is then cooled to 0° C. After stirring for 5 minutes from refluxing After addition it is stirred for 15 minutes to come to room temperature washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine dried (MgSO4) concentrated to dryness The residue is purified by column chromatography

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 2-phenylethanol (9.09 g; 72.9 mmol) dissolved in THF (75 ml) and cooled to 0° C. is added NaH (60%; 3.5 g; 87 mmol) in portions over 10 minutes. The mixture is allowed to warm to room temperature, stirred for 45 minutes and cooled. Allyl bromide (6.3 ml; 73 mmol) is added and the mixture is brought to room temperature and stirred vigorously. The reaction mixture is heated at 45° C. for 3 hours, quenched with MeOH, diluted with Et2O, washed with H2O 3× and brine, dried (MgSO4) and concentrated to dryness. The resultant yellow oil is purified by column chromatography using 10% ether/petroleum ether to give 2-allyloxyethylbenzene as a clear oil which is used directly in Step B. to warm to room temperature cooled is brought to room temperature stirred vigorously The reaction mixture is heated at 45° C. for 3 hours quenched with MeOH diluted with Et2O washed with H2O 3× and brine dried (MgSO4) concentrated to dryness The resultant yellow oil is purified by column chromatography

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: To a cooled (0° C.) solution of 2-allyloxyethylbenzene (5. g; 30.8 mmol) dissolved in THF (75 ml) is slowly added a 0.5M THF solution of 9-BBN [9-borabicyclo [3.3.1]nonane] (68 ml; 34 mmol) and the reaction mixture warmed to room temperature and stirred for 4 hours. The reaction mixture is then cooled to 0° C. and 5 ml H2O is added followed by slow addition of 6N NaOH (30 ml; 7.2 g/30 ml). After stirring for 5 minutes, 30% H2O2 (20 ml) is added over 15 min. The reaction mixture warms significantly but is kept from refluxing. After addition is complete, it is stirred for 15 minutes allowing the mixture to come to room temperature. It is then diluted with. Et2O, washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine, dried (MgSO4) and concentrated to dryness. The residue is purified by column chromatography using Et2O to obtain 3-(2-phenylethoxy)-1-propanol which is used directly in Step C. The reaction mixture is then cooled to 0° C. After stirring for 5 minutes from refluxing After addition it is stirred for 15 minutes to come to room temperature It is then diluted with Et2O, washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine dried (MgSO4) concentrated to dryness The residue is purified by column chromatography

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

实验步骤: To a cooled (0° C.) solution of 2-allyloxyethylbenzene (5. g; 30.8 mmol) dissolved in THF (75 ml) is slowly added a 0.5M THF solution of 9-BBN [9-borabicyclo [3.3.1]nonane] (68 ml; 34 mmol) and the reaction mixture warmed to room temperature and stirred for 4 hours. The reaction mixture is then cooled to 0° C. and 5 ml H2O is added followed by slow addition of 6N NaOH (30 ml; 7.2 g/30 ml). After stirring for 5 minutes, 30% H2O2 (20 ml) is added over 15 min. The reaction mixture warms significantly but is kept from refluxing. After addition is complete, it is stirred for 15 minutes allowing the mixture to come to room temperature. It is then diluted with. Et2O, washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine, dried (MgSO4) and concentrated to dryness. The residue is purified by column chromatography using Et2O to obtain 3-(2-phenylethoxy)-1-propanol which is used directly in Step C. The reaction mixture is then cooled to 0° C. After stirring for 5 minutes from refluxing After addition it is stirred for 15 minutes to come to room temperature It is then diluted with Et2O, washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine dried (MgSO4) concentrated to dryness The residue is purified by column chromatography

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

实验步骤: To a cooled (0° C.) solution of 2-allyloxyethylbenzene (5. g; 30.8 mmol) dissolved in THF (75 ml) is slowly added a 0.5M THF solution of 9-BBN [9-borabicyclo [3.3.1]nonane] (68 ml; 34 mmol) and the reaction mixture warmed to room temperature and stirred for 4 hours. The reaction mixture is then cooled to 0° C. and 5 ml H2O is added followed by slow addition of 6N NaOH (30 ml; 7.2 g/30 ml). After stirring for 5 minutes, 30% H2O2 (20 ml) is added over 15 min. The reaction mixture warms significantly but is kept from refluxing. After addition is complete, it is stirred for 15 minutes allowing the mixture to come to room temperature. It is then diluted with. Et2O, washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine, dried (MgSO4) and concentrated to dryness. The residue is purified by column chromatography using Et2O to obtain 3-(2-phenylethoxy)-1-propanol which is used directly in Step C. The reaction mixture is then cooled to 0° C. After stirring for 5 minutes from refluxing After addition it is stirred for 15 minutes to come to room temperature It is then diluted with Et2O, washed with H2O 2×, Na2S2O3 2×, NaHCO3 and brine dried (MgSO4) concentrated to dryness The residue is purified by column chromatography

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 2-phenylethanol (9.09 g; 72.9 mmol) dissolved in THF (75 ml) and cooled to 0° C. is added NaH (60%; 3.5 g; 87 mmol) in portions over 10 minutes. The mixture is allowed to warm to room temperature, stirred for 45 minutes and cooled. Allyl bromide (6.3 ml; 73 mmol) is added and the mixture is brought to room temperature and stirred vigorously. The reaction mixture is heated at 45° C. for 3 hours, quenched with MeOH, diluted with Et2O, washed with H2O 3× and brine, dried (MgSO4) and concentrated to dryness. The resultant yellow oil is purified by column chromatography using 10% ether/petroleum ether to give 2-allyloxyethylbenzene as a clear oil which is used directly in Step B. to warm to room temperature cooled is brought to room temperature stirred vigorously The reaction mixture is heated at 45° C. for 3 hours quenched with MeOH diluted with Et2O washed with H2O 3× and brine dried (MgSO4) concentrated to dryness The resultant yellow oil is purified by column chromatography

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 2-phenylethanol (9.09 g; 72.9 mmol) dissolved in THF (75 ml) and cooled to 0° C. is added NaH (60%; 3.5 g; 87 mmol) in portions over 10 minutes. The mixture is allowed to warm to room temperature, stirred for 45 minutes and cooled. Allyl bromide (6.3 ml; 73 mmol) is added and the mixture is brought to room temperature and stirred vigorously. The reaction mixture is heated at 45° C. for 3 hours, quenched with MeOH, diluted with Et2O, washed with H2O 3× and brine, dried (MgSO4) and concentrated to dryness. The resultant yellow oil is purified by column chromatography using 10% ether/petroleum ether to give 2-allyloxyethylbenzene as a clear oil which is used directly in Step B. to warm to room temperature cooled is brought to room temperature stirred vigorously The reaction mixture is heated at 45° C. for 3 hours quenched with MeOH diluted with Et2O washed with H2O 3× and brine dried (MgSO4) concentrated to dryness The resultant yellow oil is purified by column chromatography

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 2-phenylethanol (9.09 g; 72.9 mmol) dissolved in THF (75 ml) and cooled to 0° C. is added NaH (60%; 3.5 g; 87 mmol) in portions over 10 minutes. The mixture is allowed to warm to room temperature, stirred for 45 minutes and cooled. Allyl bromide (6.3 ml; 73 mmol) is added and the mixture is brought to room temperature and stirred vigorously. The reaction mixture is heated at 45° C. for 3 hours, quenched with MeOH, diluted with Et2O, washed with H2O 3× and brine, dried (MgSO4) and concentrated to dryness. The resultant yellow oil is purified by column chromatography using 10% ether/petroleum ether to give 2-allyloxyethylbenzene as a clear oil which is used directly in Step B. to warm to room temperature cooled is brought to room temperature stirred vigorously The reaction mixture is heated at 45° C. for 3 hours quenched with MeOH diluted with Et2O washed with H2O 3× and brine dried (MgSO4) concentrated to dryness The resultant yellow oil is purified by column chromatography

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

实验步骤: To a cooled (0° C.) solution of 2-allyloxyethylbenzene (5. g; 30.8 mmol) dissolved in THF (75 ml) is slowly added a 0.5M THF solution of 9-BBN [9-borabicyclo [3.3.1]nonane] (68 ml; 34 mmol) and the reaction mixture warmed to room temperature and stirred for 4 hours. The reaction mixture is then cooled to 0° C. and 5 ml H2O is added followed by slow addition of 6N NaOH (30 ml; 7.2 g/30 ml). After stirring for 5 minutes, 30% H2O2 (20 ml) is added over 15 min. The reaction mixture warms significantly but is kept from refluxing. After addition is complete, it is stirred for 15 minutes allowing the mixture to come to room temperature. It is then diluted with Et2O, washed with H2O 2x, Na2S2O3 2x, NaHCO3 and brine, dried (MgSO4) and concentrated to dryness. The residue is purified by column chromatography using Et2O to obtain 3-(2-phenylethoxy)-1-propanol which is used directly in Step C. The reaction mixture is then cooled to 0° C. After stirring for 5 minutes from refluxing After addition it is stirred for 15 minutes to come to room temperature washed with H2O 2x, Na2S2O3 2x, NaHCO3 and brine dried (MgSO4) concentrated to dryness The residue is purified by column chromatography

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 2-phenylethanol (9.09 g; 72.9 mmol) dissolved in THF (75 ml) and cooled to 0° C. is added NaH (60%; 3.5 g; 87 mmol) in portions over 10 minutes. The mixture is allowed to warm to room temperature, stirred for 45 minutes and cooled. Allyl bromide (6.3 ml; 73 mmol) is added and the mixture is brought to room temperature and stirred vigorously. The reaction mixture is heated at 45° C. for 3 hours, quenched with MeOH, diluted with Et2O, washed with H2O 3x and brine, dried (MgSO4) and concentrated to dryness. The resultant yellow oil is purified by column chromatography using 10% ether/petroleum ether to give 2-allyloxyethylbenzene as a clear oil which is used directly in Step B. to warm to room temperature cooled is brought to room temperature stirred vigorously The reaction mixture is heated at 45° C. for 3 hours quenched with MeOH diluted with Et2O washed with H2O 3x and brine dried (MgSO4) concentrated to dryness The resultant yellow oil is purified by column chromatography