7-phenylheptanal

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:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,2,6,6-Tetramethylpiperidine (1.54 mL) was dissolved in anhydrous THF (60 mL) and treated dropwise with 2.0 M n-BuLi (4 equiv) at −40° C. The reaction mixture was stirred at 0° C. for 0.5 h, cooled to −78° C. and treated with a solution of pyridazine (165 μL, 2.26 mmol) in THF (4 mL) immediately followed by a solution of 7-phenylheptanal (435 mg, 2.29 mmol) in THF (2 mL). The reaction mixture was stirred at −78° C. for 1 h before being quenched by the addition of 1 N HCl/EtOH/THF (2/9/9, 40 mL). The reaction mixture was diluted with EtOAc, and washed with H2O, saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. Flash chromatography (SiO2, 3×15 cm, 1% MeOH—CH2Cl2) afforded the alcohol (135 mg, 22%) as colorless oil: 1H NMR (CDCl3, 500 MHz) δ 9.12 (dd, 1H, J=1.8, 4.7 Hz), 7.49 (m, 2H), 7.26 (m, 2H), 7.17 (m, 3H), 4.97 (td, 1H, J=4.9, 8.0 Hz), 3.60 (d, 1H(—OH), J=5.4 Hz), 2.58 (t, 2H, J=7.7 Hz), 1.88 (m, 1H), 1.77 (m, 1H), 1.43 (m, 2H), 1.34 (m, 6H). cooled to −78° C. The reaction mixture was stirred at −78° C. for 1 h before being quenched by the addition of 1 N HCl/EtOH/THF (2/9/9, 40 mL) The reaction mixture was diluted with EtOAc washed with H2O, saturated aqueous NaHCO3 and saturated aqueous NaCl The organic layer was dried over Na2SO4 the solvent was removed under reduced pressure

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thiazole (21 μL, 0.29 mmol) in anhydrous THF (1.9 mL) was cooled to −78° C. and treated dropwise with 1.4 M t-BuLi (273 μL, 0.38 mmol). The reaction mixture was stirred at −78° C. for 0.5 h before a solution of 7-phenylheptanal (73 mg, 0.38 mmol) in THF (1.3 mL) was added. The reaction mixture was stirred at −78° C. for 0.5 h before being warmed to room temperature. The reaction mixture was diluted with EtOAc, and washed with H2O, saturated aqueous NaHCO3 and saturated aqueous NaCl before the organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. Flash chromatography (SiO2, 1.5×6.5 cm, 15-25% EtOAc-hexanes) afforded the title compound (50 mg, 62%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.68 (d, 1H, J=3.2 Hz), 7.24 (m, 3H), 7.14 (m, 3H), 4.96 (dd, 1H, J=4.8, 7.6 Hz), 3.09 (br s, 1H), 2.56 (t, 2H, J=7.8 Hz), 1.87 (m, 2H), 1.58 (m, 2H), 1.44 (m, 6H). was added before being warmed to room temperature washed with H2O, saturated aqueous NaHCO3 and saturated aqueous NaCl before the organic layer was dried over Na2SO4 the solvent was removed under reduced pressure

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thiazole (21 μL, 0.29 mmol) in anhydrous THF (1.9 mL) was cooled to −78° C. and treated dropwise with 1.4 M t-BuLi (273 μL, 0.38 mmol). The reaction mixture was stirred at −78° C. for 0.5 h before a solution of 7-phenylheptanal (73 mg, 0.38 mmol) in THF (1.3 mL) was added. The reaction mixture was stirred at −78° C. for 0.5 h before being warmed to room temperature. The reaction mixture was diluted with EtOAc, and washed with H2O, saturated aqueous NaHCO3 and saturated aqueous NaCl before the organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. Flash chromatography (SiO2, 1.5×6.5 cm, 15-25% EtOAc-hexanes) afforded the title compound (50 mg, 62%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.68 (d, 1H, J=3.2 Hz), 7.24 (m, 3H), 7.14 (m, 3H), 4.96 (dd, 1H, J=4.8, 7.6 Hz), 3.09 (br s, 1H), 2.56 (t, 2H, J=7.8 Hz), 1.87 (m, 2H), 1.58 (m, 2H), 1.44 (m, 6H). was added before being warmed to room temperature washed with H2O, saturated aqueous NaHCO3 and saturated aqueous NaCl before the organic layer was dried over Na2SO4 the solvent was removed under reduced pressure

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 2-(pyridin-2-yl)-oxazole (S1, 54 mg, 0.369 mmol) in THF (2 mL) was cooled to −78° C. before it was treated dropwise with 2.5 M n-BuLi (0.177 mL, 0.443 mmol). The reaction mixture was stirred at −78° C. for 20 min before 7-phenylheptanal (77 mg, 0.405 mmol) in THF (1 mL) was added dropwise. The solution was stirred for an additional 10 min at −78° C. before being warmed to room temperature. The reaction mixture was quenched with the addition of saturated aqueous NaHCO3, diluted with EtOAc and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4 and the solvent was removed under reduced pressure. Flash chromatography (SiO2, 20-70% EtOAc-hexanes) yielded the title compound (35 mg, 28%) as a colorless oil: 1H NMR (CDCl3, 500 MHz) δ 8.77 (s, 1H), 8.17 (d, 1H, J=8.0 Hz), 7.86 (t, 1H, J=8.0 Hz), 7.41 (m, 1H), 7.35-7.32 (m, 2H), 7.23 (m, 3H), 7.18 (s, 1H), 4.93 (t, 1H, J=6.5 Hz), 3.22 (br s, 1H), 2.65 (t, 2H, J=6.5 Hz), 2.01-1.98 (m, 2H), 1.68-1.66 (m, 2H), 1.44-1.42 (m, 5H); 13C NMR (CDCl3, 125 MHz) δ 160.3, 156.1, 150.2, 146.4, 143.1, 137.5, 128.8, 128.6, 126.0, 125.1, 124.9, 122.5, 66.5, 36.3, 35.8, 31.8, 29.6 (2C), 25.8. was added dropwise before being warmed to room temperature The reaction mixture was quenched with the addition of saturated aqueous NaHCO3 diluted with EtOAc the aqueous layer was extracted with EtOAc The combined organic extracts were washed with saturated aqueous NaCl dried over Na2SO4 the solvent was removed under reduced pressure

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

实验步骤: A two-phase mixture of ethyl acetate (30 mL) and water (35 mL) containing 7-phenylheptanal (5.2 g) and KCN (7.1 g) was stirred vigorously at room temperature for 24 h. The layers were separated and the aqueous phase was washed with water, dried (Na2SO4) and concentrated to yield 2-hydroxy-8-phenyloctanenitrile as an oil. The layers were separated the aqueous phase was washed with water dried (Na2SO4) concentrated

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

实验步骤: A two-phase mixture of ethyl acetate (30 mL) and water (35 mL) containing 7-phenylheptanal (5.2 g) and KCN (7.1 g) was stirred vigorously at room temperature for 24 h. The layers were separated and the aqueous phase was washed with water, dried (Na2SO4) and concentrated to yield 2-hydroxy-8-phenyloctanenitrile as an oil. The layers were separated the aqueous phase was washed with water dried (Na2SO4) concentrated

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

实验步骤: A solution of 7-phenylheptan-1-ol (5 g) in CH2Cl2 (25 mL) was added to a suspension of 1,1,1-tris(acetyloxy)1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane) in CH2Cl2 (25 mL) dropwise with ice-bath cooling. The cooling bath was removed after addition was complete and the resulting mixture was stirred at room temperature for 3 h. After addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL), the resulting mixture was stirred for 45 min and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic phases were washed with water, dried over Na2SO4 and concentrated to yield 7-phenylheptanal as an oil, which was used in the next step without further purification. cooling The cooling bath was removed after addition After addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL) the resulting mixture was stirred for 45 min the layers were separated The aqueous layer was extracted twice with CH2Cl2 the combined organic phases were washed with water dried over Na2SO4 concentrated

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

实验步骤: A solution of 7-phenylheptan-1-ol (5 g) in CH2Cl2 (25 mL) was added to a suspension of 1,1,1-tris(acetyloxy)1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane) in CH2Cl2 (25 mL) dropwise with ice-bath cooling. The cooling bath was removed after addition was complete and the resulting mixture was stirred at room temperature for 3 h. After addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL), the resulting mixture was stirred for 45 min and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic phases were washed with water, dried over Na2SO4 and concentrated to yield 7-phenylheptanal as an oil, which was used in the next step without further purification. cooling The cooling bath was removed after addition After addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL) the resulting mixture was stirred for 45 min the layers were separated The aqueous layer was extracted twice with CH2Cl2 the combined organic phases were washed with water dried over Na2SO4 concentrated

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir: