3-but-3-enylbenzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(but-3-en-1-yl)benzaldehyde (300 mg, 1.873 mmol) in MeOH (5 mL) was added sodium borohydride (142 mg, 3.75 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 (3-(but-3-en-1-yl)phenyl)methanol (167 mg, 1.029 mmol, 55.0% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.45-7.10 (m, 4H), 5.88 (ddt, J=17.0, 10.4, 6.5 Hz, 1H), 5.15-4.94 (m, 2H), 4.70 (br. s., 2H), 2.84-2.71 (m, 2H), 2.48-2.34 (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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(but-3-en-1-yl)benzaldehyde (300 mg, 1.873 mmol) in MeOH (5 mL) was added sodium borohydride (142 mg, 3.75 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 (3-(but-3-en-1-yl)phenyl)methanol (167 mg, 1.029 mmol, 55.0% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.45-7.10 (m, 4H), 5.88 (ddt, J=17.0, 10.4, 6.5 Hz, 1H), 5.15-4.94 (m, 2H), 4.70 (br. s., 2H), 2.84-2.71 (m, 2H), 2.48-2.34 (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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-bromo-3-(but-3-en-1-yl)benzene (0.5 g, 2.369 mmol) in tetrahydrofuran (10 mL) at −78° C. was added BuLi (1.137 mL, 2.84 mmol) dropwise. It was then stirred at this temperature for 1 h, then N,N-dimethylformamide (0.208 g, 2.84 mmol) was added. The reaction mixture was stirred at −78° C. for 30 min, then rt for 3 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was dried over MgSO4, filtered and concentrated to obtain 3-(but-3-en-1-yl)benzaldehyde (0.3 g, 79%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.03 (s, 1H), 7.77-7.72 (m, 2H), 7.51-7.46 (m, 2H), 5.86 (ddt, J=17.1, 10.3, 6.6 Hz, 1H), 5.10-5.00 (m, 2H), 2.86-2.79 (m, 2H), 2.48-2.39 (m, 2H). The reaction mixture was stirred at −78° C. for 30 min rt for 3 h It was then quenched with NH4Cl extracted with ether The organic layer was dried over MgSO4 filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(but-3-en-1-yl)benzaldehyde (300 mg, 1.873 mmol) in MeOH (5 mL) was added sodium borohydride (142 mg, 3.75 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 (3-(but-3-en-1-yl)phenyl)methanol (167 mg, 1.029 mmol, 55.0% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.45-7.10 (m, 4H), 5.88 (ddt, J=17.0, 10.4, 6.5 Hz, 1H), 5.15-4.94 (m, 2H), 4.70 (br. s., 2H), 2.84-2.71 (m, 2H), 2.48-2.34 (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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-bromo-3-(but-3-en-1-yl)benzene (0.5 g, 2.369 mmol) in tetrahydrofuran (10 mL) at −78° C. was added BuLi (1.137 mL, 2.84 mmol) dropwise. It was then stirred at this temperature for 1 h, then N,N-dimethylformamide (0.208 g, 2.84 mmol) was added. The reaction mixture was stirred at −78° C. for 30 min, then rt for 3 h. It was then quenched with NH4Cl, extracted with ether. The organic layer was dried over MgSO4, filtered and concentrated to obtain 3-(but-3-en-1-yl)benzaldehyde (0.3 g, 79%) as an oil. 1H NMR (400 MHz, CDCl3) δ 10.03 (s, 1H), 7.77-7.72 (m, 2H), 7.51-7.46 (m, 2H), 5.86 (ddt, J=17.1, 10.3, 6.6 Hz, 1H), 5.10-5.00 (m, 2H), 2.86-2.79 (m, 2H), 2.48-2.39 (m, 2H). The reaction mixture was stirred at −78° C. for 30 min rt for 3 h It was then quenched with NH4Cl extracted with ether The organic layer was dried over MgSO4 filtered concentrated