1-phenyldecane-1,3-dione

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound was prepared as described above for the preparation of Example 2, from 102 mg (0.28 mmol) of Intermediate 45 and 69 mg (0.28 mmol) of Intermediate 19 to yield 77 mg of Example 45: TLC (EtOAc/MeOH , 713): Rf=0.56; 1H NMR (DMSO-d6, 400 MHz) δ11.55 (d, 1H, J=9.6), 7.86 (d, 2H, J=6.8), 7.76 (d, 2H, J=6.4), 7.46. (m, 3H), 7.38 (m, 3H), 7.10 (d, 2H, J=8.4), 6.78 (d, 2H, J=8.4), 5.5 (s, 1H), 4.10 (t, 2H, J=6.6), 4.0 (m, 1H), 3.16 (m, 1H), 2.86 (t, 2H, J=6.5), 2.69 (dd, 1H, J=13.6, 9.6), 2.31 (s, 3H), 1.87 (m, 2H), 1.25-1.1 (m, 10H), 0.78 (t, 3H, J=6.8); low resolution MS (ES+)m/e 595.1 (MH+).

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1 g (6.1 mmol) of benzoylacetone in 6 mL of THF at −78° C. was added 8.2 mL (12.3 mmol) of a 1.5 M LDA solution in THF. Warmed to 0° C. over 2 h, then 2.6 mL (12.3 mmol) of 1-iodohexane was added. The mixture was stirred at rt for 3 h before quenching with saturated aqueous NH4Cl solution and dilution with Et2O. The organics were dried (Na2SO4), filtered, concentrated, and purified by silica gel chromatography (15/1 hexanes/Et2O) to yield Intermediate 19: TLC Rf=0.52 (1/10 Et2O/Hexanes); 1H NMR (400 MHz, CDCl3, enol form) δ7.88 (m, 2H), 7.54-7.43 (m, 3H), 6.17 (s, 1H), 2.42 (t, 2H, J=7.6), 1.66 (m, 2H), 1.4-1.25 (m, 8H), 0.85 (m, 3H); low resolution MS(ES+) m/e 269.0 (M+Na+). before quenching with saturated aqueous NH4Cl solution and dilution with Et2O The organics were dried (Na2SO4) filtered concentrated purified by silica gel chromatography (15/1 hexanes/Et2O)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1 g (6.1 mmol) of benzoylacetone in 6 mL of THF at −78° C. was added 8.2 mL (12.3 mmol) of a 1.5 M LDA solution in THF. Warmed to 0° C. over 2 h, then 2.6 mL (12.3 mmol) of 1-iodohexane was added. The mixture was stirred at rt for 3 h before quenching with saturated aqueous NH4Cl solution and dilution with Et2O. The organics were dried (Na2SO4), filtered, concentrated, and purified by silica gel chromatography (15/1 hexanes/Et2O) to yield Intermediate 19: TLC Rf=0.52 (1/10 Et2O/Hexanes); 1H NMR (400 MHz, CDCl3, enol form) δ7.88 (m, 2H), 7.54-7.43 (m, 3H), 6.17 (s, 1H), 2.42 (t, 2H, J=7.6), 1.66 (m, 2H), 1.4-1.25 (m, 8H), 0.85 (m, 3H); low resolution MS(ES+) m/e 269.0 (M+Na+). before quenching with saturated aqueous NH4Cl solution and dilution with Et2O The organics were dried (Na2SO4) filtered concentrated purified by silica gel chromatography (15/1 hexanes/Et2O)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1 g (6.1 mmol) of benzoylacetone in 6 mL of THF at −78° C. was added 8.2 mL (12.3 mmol) of a 1.5 M LDA solution in THF. Warmed to 0° C. over 2 h, then 2.6 mL (12.3 mmol) of 1-iodohexane was added. The mixture was stirred at rt for 3 h before quenching with saturated aqueous NH4Cl solution and dilution with Et2O. The organics were dried (Na2SO4), filtered, concentrated, and purified by silica gel chromatography (15/1 hexanes/Et2O) to yield Intermediate 19: TLC Rf=0.52 (1/10 Et2O/Hexanes); 1H NMR (400 MHz, CDCl3, enol form) δ7.88 (m, 2H), 7.54-7.43 (m, 3H), 6.17 (s, 1H), 2.42 (t, 2H, J=7.6), 1.66 (m, 2H), 1.4-1.25 (m, 8H), 0.85 (m, 3H); low resolution MS(ES+) m/e 269.0 (M+Na+). before quenching with saturated aqueous NH4Cl solution and dilution with Et2O The organics were dried (Na2SO4) filtered concentrated purified by silica gel chromatography (15/1 hexanes/Et2O)