6-cyclohexylhexan-1-ol

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a solution of 6-cyclohexyl-hexan-1-ol (0.98 g, 5.3 mmol) in DMF (15 mL) was added triphenylphosphine (1.56 g, 5.9 mmol). The solution was cooled to 0° C. and NBS (1.02 g, 5.7 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.6 mL). The solution was diluted with ether (80 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford (6-bromo-hexyl)-cyclohexane (1.16 g, 89%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.41 (2H, t, J=7.2 Hz), 1.85 (2H, m), 1.66 (5H, m), 1.42 (2H, m), 1.08–1.36 (10H, m), 0.88 (2H, m); 13C NMR (75 MHz, CDCl3) δ 37.91, 37.68, 34.37, 33.72, 33.14, 29.39, 28.51, 27.04, 26.96, 26.73. the reaction was quenched with methanol (0.6 mL) The solution was diluted with ether (80 mL) washed with water, saturated aqueous NaHCO3 and brine successively The organic layer was dried concentrated The residue was purified by flash chromatography on silica gel eluting with hexane

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

実験手順: A solution of 6-cyclohexylidene-hexan-1-ol (1.05 g, 5.77 mmol) in MEOH (40 mL) was hydrogenated with Pd—C (0.23 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 6-cyclohexyl-hexan-1-ol (1.02 g, 96%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.63 (2H, t, J=6.6 Hz), 1.46–1.80 (7H, m), 1.04–1.44 (12H, m), 0.86 (2H, m); 13C NMR (75 MHz, CDCl3) δ 63.33, 37.92, 37.74, 33.72, 33.08, 30.04, 27.10, 27.04, 26.73, 26.05. The catalyst was removed by filtration the filtrate was evaporated under reduced pressure

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

実験手順: To a solution of 6-cyclohexyl-hexan-1-ol (0.98 g, 5.3 mmol) in DMF (15 mL) was added triphenylphosphine (1.56 g, 5.9 mmol). The solution was cooled to 0° C. and NBS (1.02 g, 5.7 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.6 mL). The solution was diluted with ether (80 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford (6-bromo-hexyl)-cyclohexane (1.16 g, 89%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.41 (2H, t, J=7.2 Hz), 1.85 (2H, m), 1.66 (5H, m), 1.42 (2H, m), 1.08–1.36 (10H, m), 0.88 (2H, m); 13C NMR (75 MHz, CDCl3) δ 37.91, 37.68, 34.37, 33.72, 33.14, 29.39, 28.51, 27.04, 26.96, 26.73. the reaction was quenched with methanol (0.6 mL) The solution was diluted with ether (80 mL) washed with water, saturated aqueous NaHCO3 and brine successively The organic layer was dried concentrated The residue was purified by flash chromatography on silica gel eluting with hexane

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

実験手順: A solution of 6-cyclohexylidene-hexan-1-ol (1.05 g, 5.77 mmol) in MEOH (40 mL) was hydrogenated with Pd—C (0.23 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 6-cyclohexyl-hexan-1-ol (1.02 g, 96%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.63 (2H, t, J=6.6 Hz), 1.46–1.80 (7H, m), 1.04–1.44 (12H, m), 0.86 (2H, m); 13C NMR (75 MHz, CDCl3) δ 63.33, 37.92, 37.74, 33.72, 33.08, 30.04, 27.10, 27.04, 26.73, 26.05. The catalyst was removed by filtration the filtrate was evaporated under reduced pressure

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

実験手順: To a solution of 6-cyclohexyl-hexan-1-ol (0.98 g, 5.3 mmol) in DMF (15 mL) was added triphenylphosphine (1.56 g, 5.9 mmol). The solution was cooled to 0° C. and NBS (1.02 g, 5.7 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.6 mL). The solution was diluted with ether (80 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford (6-bromo-hexyl)-cyclohexane (1.16 g, 89%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.41 (2H, t, J=7.2 Hz), 1.85 (2H, m), 1.66 (5H, m), 1.42 (2H, m), 1.08–1.36 (10H, m), 0.88 (2H, m); 13C NMR (75 MHz, CDCl3) δ 37.91, 37.68, 34.37, 33.72, 33.14, 29.39, 28.51, 27.04, 26.96, 26.73. the reaction was quenched with methanol (0.6 mL) The solution was diluted with ether (80 mL) washed with water, saturated aqueous NaHCO3 and brine successively The organic layer was dried concentrated The residue was purified by flash chromatography on silica gel eluting with hexane

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

実験手順: A solution of 6-cyclohexylidene-hexan-1-ol (1.05 g, 5.77 mmol) in MEOH (40 mL) was hydrogenated with Pd—C (0.23 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 6-cyclohexyl-hexan-1-ol (1.02 g, 96%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.63 (2H, t, J=6.6 Hz), 1.46–1.80 (7H, m), 1.04–1.44 (12H, m), 0.86 (2H, m); 13C NMR (75 MHz, CDCl3) δ 63.33, 37.92, 37.74, 33.72, 33.08, 30.04, 27.10, 27.04, 26.73, 26.05. The catalyst was removed by filtration the filtrate was evaporated under reduced pressure