4-烯丙氧基苯甲醛

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:; See reaction.notes.procedure_details.

实验步骤: To a solution of 4-allyloxybenzaldehyde (1.0 g, 6.17 mmol) in acetone (40 mL) and water (5 mL) is added a 2.5% solution of OsO4 in tert. butanol (1.25 mL) followed by N-methyl morpholine-N-oxide (867 mg, 7.4 mmol). The pale yellow solution is stirred at it for 6 h, diluted with EA (250 mL) and washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL). The washings are extracted with EA (150 mL). The combined organic extracts are concentrated and purified by column chromatography on silica gel to give the title compound (731 mg) as a turbid oil. The title compound reversibly polymerizes upon standing. LC-MS: tR=0.58 min, [M+1+CH3CN]+=238. washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL) The washings are extracted with EA (150 mL) The combined organic extracts are concentrated purified by column chromatography on silica gel

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

实验步骤: To a solution of 4-allyloxybenzaldehyde (1.0 g, 6.17 mmol) in acetone (40 mL) and water (5 mL) is added a 2.5% solution of OsO4 in tert. butanol (1.25 mL) followed by N-methyl morpholine-N-oxide (867 mg, 7.4 mmol). The pale yellow solution is stirred at it for 6 h, diluted with EA (250 mL) and washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL). The washings are extracted with EA (150 mL). The combined organic extracts are concentrated and purified by column chromatography on silica gel to give the title compound (731 mg) as a turbid oil. The title compound reversibly polymerizes upon standing. LC-MS: tR=0.58 min, [M+1+CH3CN]+=238. washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL) The washings are extracted with EA (150 mL) The combined organic extracts are concentrated purified by column chromatography on silica gel

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

实验步骤: 4-allyloxybenzaldehyde was prepared by reaction of allyl bromide on 4-hydroxybenzaldehyde in refluxing acetone in the presence of K2CO3. The distilled product was used as a precursor for 4-allyloxystyrene synthesis.

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

实验步骤: The reaction conditions taught by A. E. Moormann, Syn. Comm., 23(6), 789-795 (1993) were used in the following preparation. To a stirred solution of 4.8 grams (0.030 mole) of ethyl piperidin-4-ylcarboxylate and 4.9 grams (0.030 mole) of 4-(2-propen-1-yloxy)benzaldehyde in 50 mL of ethanol was added 3.8 mL (0.030 mole) of borane-pyridine complex. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 18 hours. The reaction mixture was then taken up in water and extracted with methylene chloride. The organic layer was washed with water and dried with magnesium sulfate. The mixture was filtered and the filtrate concentrated under reduced pressure, yielding 9.0 grams of ethyl N-[4-(2-propen-1-yloxy)phenylmethyl]piperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure. The reaction conditions , 23(6), 789-795 (1993) were used in the following preparation Upon completion of addition extracted with methylene chloride The organic layer was washed with water dried with magnesium sulfate The mixture was filtered the filtrate concentrated under reduced pressure

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

实验步骤: To a solution of 4-allyloxybenzaldehyde (1.0 g, 6.17 mmol) in acetone (40 mL) and water (5 mL) is added a 2.5% solution of OsO4 in tert. butanol (1.25 mL) followed by N-methyl morpholine-N-oxide (867 mg, 7.4 mmol). The pale yellow solution is stirred at it for 6 h, diluted with EA (250 mL) and washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL). The washings are extracted with EA (150 mL). The combined organic extracts are concentrated and purified by column chromatography on silica gel to give the title compound (731 mg) as a turbid oil. The title compound reversibly polymerizes upon standing. LC-MS: tR=0.58 min, [M+1+CH3CN]+=238. washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL) The washings are extracted with EA (150 mL) The combined organic extracts are concentrated purified by column chromatography on silica gel

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

实验步骤: To a solution of 4-allyloxybenzaldehyde (1.0 g, 6.17 mmol) in acetone (40 mL) and water (5 mL) is added a 2.5% solution of OsO4 in tert. butanol (1.25 mL) followed by N-methyl morpholine-N-oxide (867 mg, 7.4 mmol). The pale yellow solution is stirred at rt for 6 h, diluted with EA (250 mL) and washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL). The washings are extracted with EA (150 mL). The combined organic extracts are concentrated and purified by column chromatography on silica gel to give the title compound (731 mg) as a turbid oil. The title compound reversibly polymerizes upon standing. LC-MS: tR=0.58 min, [M+1+CH3CN]+=238. washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL) The washings are extracted with EA (150 mL) The combined organic extracts are concentrated purified by column chromatography on silica gel

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 solution of 4-allyloxybenzaldehyde (1.0 g, 6.17 mmol) in acetone (40 mL) and water (5 mL) is added a 2.5% solution of OsO4 in tert. butanol (1.25 mL) followed by N-methyl morpholine-N-oxide (867 mg, 7.4 mmol). The pale yellow solution is stirred at rt for 6 h, diluted with EA (250 mL) and washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL). The washings are extracted with EA (150 mL). The combined organic extracts are concentrated and purified by column chromatography on silica gel to give the title compound (731 mg) as a turbid oil. The title compound reversibly polymerizes upon standing. LC-MS: tR=0.58 min, [M+1+CH3CN]+=238. washed with 10% aq. citric acid solution (100 mL) and water (2×100 mL) The washings are extracted with EA (150 mL) The combined organic extracts are concentrated purified by column chromatography on silica gel

实验步骤: 投料: 将SM191.0eq)溶解在甲醇中，在冰浴下加入硼氢化钠(2.0eq)（分批少量）保持温度在0℃搅拌2h，缓慢升至室温搅拌4h 16:30 点板TLC（DCM:MEOH=20:1)对比原料点有极性变小的新点 17：30 加入氯化铵溶液淬灭反应，用DCM萃取三次，合并有机相用饱和氯化钠溶液洗涤和无水硫酸钠干燥，减压蒸馏浓缩用于下一步。