2-丁-3-烯基苯甲醛

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

实验步骤: A mixture of 2-(but-3-en-1-yl)benzaldehyde (500 mg, 3.12 mmol) in MeOH (10 mL) was added NaBH4 (118 mg, 3.12 mmol) and the mixture was stirred at rt for 1 h. It was then added water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to obtain (2-(but-3-en-1-yl)phenyl)methanol (320 mg, 1.973 mmol, 63.2% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.44-7.37 (m, 1H), 7.33-7.21 (m, 3H), 5.91 (ddt, J=16.9, 10.2, 6.6 Hz, 1H), 5.13-4.99 (m, 2H), 4.76 (d, J=5.9 Hz, 2H), 2.86-2.77 (m, 2H), 2.44-2.35 (m, 2H). added water, extracted with EtOAc The organic layer was dried over MgSO4 filtered concentrated to obtain an oil, which was then purified by biotage eluting with 10% EtOAc/hexane

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

实验步骤: To a mixture of 1-bromo-2-(but-3-en-1-yl)benzene (1 g, 4.74 mmol) in THF (15 mL) at −78° C. was added BuLi (2.274 mL, 5.68 mmol) dropwise. It was stirred at this temperature for 1 h, then N,N-dimethylformamide (0.416 g, 5.68 mmol) was added and stirred at −78° C. for 30 min. then warmed up to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was then dried over MgSO4, filtered and concentrated to obtain 2-(but-3-en-1-yl)benzaldehyde (0.7 g, 92%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.35-10.26 (m, 1H), 7.86 (dd, J=7.6, 1.5 Hz, 1H), 7.54 (td, J=7.5, 1.6 Hz, 1H), 7.44-7.38 (m, 1H), 7.30 (d, J=8.1 Hz, 1H), 5.95-5.83 (m, 1H), 5.09-5.00 (m, 2H),), 3.20-3.12 (m, 2H), 2.44-2.36 (m, 2H). stirred at −78° C. for 30 min. stirred at rt for 1 h It was then quenched with NH4Cl extracted with ether The organic layer was then dried over MgSO4 filtered concentrated

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

实验步骤: To a mixture of 1-bromo-2-(but-3-en-1-yl)benzene (1 g, 4.74 mmol) in THF (15 mL) at −78° C. was added BuLi (2.274 mL, 5.68 mmol) dropwise. It was stirred at this temperature for 1 h, then N,N-dimethylformamide (0.416 g, 5.68 mmol) was added and stirred at −78° C. for 30 min. then warmed up to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was then dried over MgSO4, filtered and concentrated to obtain 2-(but-3-en-1-yl)benzaldehyde (0.7 g, 92%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.35-10.26 (m, 1H), 7.86 (dd, J=7.6, 1.5 Hz, 1H), 7.54 (td, J=7.5, 1.6 Hz, 1H), 7.44-7.38 (m, 1H), 7.30 (d, J=8.1 Hz, 1H), 5.95-5.83 (m, 1H), 5.09-5.00 (m, 2H),), 3.20-3.12 (m, 2H), 2.44-2.36 (m, 2H). stirred at −78° C. for 30 min. stirred at rt for 1 h It was then quenched with NH4Cl extracted with ether The organic layer was then dried over MgSO4 filtered concentrated

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

实验步骤: A mixture of 2-(but-3-en-1-yl)benzaldehyde (500 mg, 3.12 mmol) in MeOH (10 mL) was added NaBH4(118 mg, 3.12 mmol) and the mixture was stirred at rt for 1 h. It was then added water, extracted with EtOAc. The organic was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to obtain (2-(but-3-en-1-yl)phenyl)methanol (320 mg, 1.973 mmol, 63.2% yield) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.44-7.37 (m, 1H), 7.33-7.21 (m, 3H), 5.91 (ddt, J=16.9, 10.2, 6.6 Hz, 1H), 5.13-4.99 (m, 2H), 4.76 (d, J=5.9 Hz, 2H), 2.86-2.77 (m, 2H), 2.44-2.35 (m, 2H). added water, extracted with EtOAc The organic was dried over MgSO4 filtered concentrated to obtain an oil, which was then purified by biotage eluting with 10% EtOAc/hexane

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

实验步骤: A mixture of 2-(but-3-en-1-yl)benzaldehyde (500 mg, 3.12 mmol) in MeOH (10 mL) was added NaBH4(118 mg, 3.12 mmol) and the mixture was stirred at rt for 1 h. It was then added water, extracted with EtOAc. The organic was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to obtain (2-(but-3-en-1-yl)phenyl)methanol (320 mg, 1.973 mmol, 63.2% yield) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.44-7.37 (m, 1H), 7.33-7.21 (m, 3H), 5.91 (ddt, J=16.9, 10.2, 6.6 Hz, 1H), 5.13-4.99 (m, 2H), 4.76 (d, J=5.9 Hz, 2H), 2.86-2.77 (m, 2H), 2.44-2.35 (m, 2H). added water, extracted with EtOAc The organic was dried over MgSO4 filtered concentrated to obtain an oil, which was then purified by biotage eluting with 10% EtOAc/hexane

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

实验步骤: To a mixture of 1-bromo-2-(but-3-en-1-yl)benzene (1 g, 4.74 mmol) in THF (10 mL) at −78° C. was added BuLi (2.274 mL, 5.68 mmol) dropwise. It was then stirred at this temperature for 1 h, then N,N-dimethylformamide (0.416 g, 5.68 mmol) was added. The reaction was stirred at 78° C. for 30 min, then warmed to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was then dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 10% EtOAc/hexane to obtain 2-(but-3-en-1-yl)benzaldehyde (0.7 g, 92%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.35-10.26 (m, 1H), 7.86 (dd, J=7.6, 1.5 Hz, 1H), 7.54 (td, J=7.5, 1.6 Hz, 1H), 7.44-7.38 (m, 1H), 7.30 (d, J=8.1 Hz, 1H), 5.95-5.83 (m, 1H), 5.09-5.00 (m, 2H),), 3.20-3.12 (m, 2H), 2.44-2.36 (m, 2H). The reaction was stirred at 78° C. for 30 min stirred at rt for 1 h It was then quenched with NH4Cl extracted with ether The organic layer was then dried over MgSO4 filtered concentrated The residue was purified by biotage eluting with 10% EtOAc/hexane

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

实验步骤: A mixture of 2-(but-3-en-1-yl)benzaldehyde (500 mg, 3.12 mmol) in MeOH (10 mL) was added NaBH4 (118 mg, 3.12 mmol) and the mixture was stirred at rt for 1 h. It was then added water, extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to obtain (2-(but-3-en-1-yl)phenyl)methanol (320 mg, 1.973 mmol, 63.2% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.44-7.37 (m, 1H), 7.33-7.21 (m, 3H), 5.91 (ddt, J=16.9, 10.2, 6.6 Hz, 1H), 5.13-4.99 (m, 2H), 4.76 (d, J=5.9 Hz, 2H), 2.86-2.77 (m, 2H), 2.44-2.35 (m, 2H). added water, extracted with EtOAc The organic layer was dried over MgSO4 filtered concentrated to obtain an oil, which was then purified by biotage eluting with 10% EtOAc/hexane

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

实验步骤: To a mixture of 1-bromo-2-(but-3-en-1-yl)benzene (1 g, 4.74 mmol) in THF (15 mL) at −78° C. was added BuLi (2.274 mL, 5.68 mmol) dropwise. It was stirred at this temperature for 1 h, then N,N-dimethylformamide (0.416 g, 5.68 mmol) was added and stirred at −78° C. for 30 min. then warmed up to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was then dried over MgSO4, filtered and concentrated to obtain 2-(but-3-en-1-yl)benzaldehyde (0.7 g, 92%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.35-10.26 (m, 1H), 7.86 (dd, J=7.6, 1.5 Hz, 1H), 7.54 (td, J=7.5, 1.6 Hz, 1H), 7.44-7.38 (m, 1H), 7.30 (d, J=8.1 Hz, 1H), 5.95-5.83 (m, 1H), 5.09-5.00 (m, 2H),), 3.20-3.12 (m, 2H), 2.44-2.36 (m, 2H). stirred at −78° C. for 30 min. stirred at rt for 1 h It was then quenched with NH4Cl extracted with ether The organic layer was then dried over MgSO4 filtered concentrated

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

实验步骤: A mixture of 2-(but-3-en-1-yl)benzaldehyde (500 mg, 3.12 mmol) in MeOH (10 mL) was added NaBH4(118 mg, 3.12 mmol) and the mixture was stirred at rt for 1 h. It was then added water, extracted with EtOAc. The organic was dried over MgSO4, filtered and concentrated to obtain an oil, which was then purified by biotage, eluting with 10% EtOAc/hexane to obtain (2-(but-3-en-1-yl)phenyl)methanol (320 mg, 1.973 mmol, 63.2% yield) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.44-7.37 (m, 1H), 7.33-7.21 (m, 3H), 5.91 (ddt, J=16.9, 10.2, 6.6 Hz, 1H), 5.13-4.99 (m, 2H), 4.76 (d, J=5.9 Hz, 2H), 2.86-2.77 (m, 2H), 2.44-2.35 (m, 2H). added water, extracted with EtOAc The organic was dried over MgSO4 filtered concentrated to obtain an oil, which was then purified by biotage eluting with 10% EtOAc/hexane

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

实验步骤: To a mixture of 1-bromo-2-(but-3-en-1-yl)benzene (1 g, 4.74 mmol) in THF (10 mL) at −78° C. was added BuLi (2.274 mL, 5.68 mmol) dropwise. It was then stirred at this temperature for 1 h, then N,N-dimethylformamide (0.416 g, 5.68 mmol) was added. The reaction was stirred at 78° C. for 30 min, then warmed to rt and stirred at rt for 1 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was then dried over MgSO4, filtered and concentrated. The residue was purified by biotage, eluting with 10% EtOAc/hexane to obtain 2-(but-3-en-1-yl)benzaldehyde (0.7 g, 92%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.35-10.26 (m, 1H), 7.86 (dd, J=7.6, 1.5 Hz, 1H), 7.54 (td, J=7.5, 1.6 Hz, 1H), 7.44-7.38 (m, 1H), 7.30 (d, J=8.1 Hz, 1H), 5.95-5.83 (m, 1H), 5.09-5.00 (m, 2H),), 3.20-3.12 (m, 2H), 2.44-2.36 (m, 2H). The reaction was stirred at 78° C. for 30 min stirred at rt for 1 h It was then quenched with NH4Cl extracted with ether The organic layer was then dried over MgSO4 filtered concentrated The residue was purified by biotage eluting with 10% EtOAc/hexane