[(E)-3-bromoprop-1-enyl]cyclohexane

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

実験手順: To a stirred solution of (E)-3-cyclohexyl-2-propen-1-ol (A. G. M. Barrett et al, Tetrahedron, 1996, 52, 15325), (1.47 g, 10.5 mmol) in diethyl ether (20 ml) and pyridine (1 ml) was added phosphorus tribromide (1.40 ml, 15 mmol) dropwise at room temperature under an atmosphere of nitrogen. After 16 h, the reaction mixture was carefully poured onto ice water (100 ml) and extracted with diethyl ether (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by silica (20 g) column chromatography eluting with hexane:ethyl acetate (4:1) to give the title compound as a colourless oil (1.3 g, 61%). the reaction mixture was carefully poured onto ice water (100 ml) extracted with diethyl ether (100 ml) The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) dried (MgSO4) concentrated in vacuo to give the crude product This was purified by silica (20 g) column chromatography eluting with hexane:ethyl acetate (4:1)

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

実験手順: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 (m, 6 H) 1.69 (m, 4 H) 1.98 (m, 1 H) 3.94 (m, 2 H) 5.65 (m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo

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

実験手順: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 (m, 6 H) 1.69 (m, 4 H) 1.98 (m, 1 H) 3.94 (m, 2 H) 5.65 (m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo

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

実験手順: To a stirred solution of (E)-3-cyclohexyl-2-propen-1-ol (A. G. M. Barrett et al, Tetrahedron, 1996, 52, 15325), (1.47 g, 10.5 mmol) in diethyl ether (20 ml) and pyridine (1 ml) was added phosphorus tribromide (1.40 ml, 15 mmol) dropwise at room temperature under an atmosphere of nitrogen. Afler 16 h, the reaction mixture was carefully poured onto ice water (100 ml) and extracted with diethyl ether (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by silica (20 g) column chromatography cluting with hexane:ethyl acetate (4:1) to give the title compound as a colourless oil (1.3 g, 61%). Afler 16 h, the reaction mixture was carefully poured onto ice water (100 ml) extracted with diethyl ether (100 ml) The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) dried (MgSO4) concentrated in vacuo to give the crude product This was purified by silica (20 g) column chromatography

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

実験手順: To a stirred solution of (E)-3-cyclohexyl-2-propen-1-ol (A. G. M. Barrett et al, Tetrahedron, 1996, 52, 15325), (1.47 g, 10.5 mmol) in diethyl ether (20 ml) and pyridine (1 ml) was added phosphorus tribromide (1.40 ml, 15 mmol) dropwise at room temperature under an atmosphere of nitrogen. Afler 16 h, the reaction mixture was carefully poured onto ice water (100 ml) and extracted with diethyl ether (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by silica (20 g) column chromatography cluting with hexane:ethyl acetate (4:1) to give the title compound as a colourless oil (1.3 g, 61%). Afler 16 h, the reaction mixture was carefully poured onto ice water (100 ml) extracted with diethyl ether (100 ml) The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) dried (MgSO4) concentrated in vacuo to give the crude product This was purified by silica (20 g) column chromatography

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

実験手順: To a stirred solution of (E)-3-cyclohexyl-2-propen-1-ol (A. G. M. Barrett et al, Tetrahedron, 1996, 52, 15325), (1.47 g, 10.5 mmol) in diethyl ether (20 ml) and pyridine (1 ml) was added phosphorus tribromide (1.40 ml, 15 mmol) dropwise at room temperature under an atmosphere of nitrogen. After 16 h, the reaction mixture was carefully poured onto ice water (100 ml) and extracted with diethyl ether (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by silica (20 g) column chromatography eluting with hexane:ethyl acetate (4:1) to give the title compound as a colourless oil (1.3 g, 61%). the reaction mixture was carefully poured onto ice water (100 ml) extracted with diethyl ether (100 ml) The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) dried (MgSO4) concentrated in vacuo to give the crude product This was purified by silica (20 g) column chromatography eluting with hexane:ethyl acetate (4:1)

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

実験手順: To a stirred solution of (E)-3-cyclohexyl-2-propen-1-ol (A. G. M. Barrett et al, Tetrahedron, 1996, 52, 15325), (1.47 g, 10.5 mmol) in diethyl ether (20 ml) and pyridine (1 ml) was added phosphorus tribromide (1.40 ml, 15 mmol) dropwise at room temperature under an atmosphere of nitrogen. After 16 h, the reaction mixture was carefully poured onto ice water (100 ml) and extracted with diethyl ether (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by silica (20 g) column chromatography eluting with hexane:ethyl acetate (4:1) to give the title compound as a colourless oil (1.3 g, 61%). the reaction mixture was carefully poured onto ice water (100 ml) extracted with diethyl ether (100 ml) The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) dried (MgSO4) concentrated in vacuo to give the crude product This was purified by silica (20 g) column chromatography eluting with hexane:ethyl acetate (4:1)

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

実験手順: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 (m, 6 H) 1.69 (m, 4 H) 1.98 (m, 1 H) 3.94 (m, 2 H) 5.65 (m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo

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

実験手順: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 m, 6 H) 1.69 m, 4 H) 1.98 m, 1 H) 3.94 m, 2 H) 5.65 m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo

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

実験手順: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 m, 6 H) 1.69 m, 4 H) 1.98 m, 1 H) 3.94 m, 2 H) 5.65 m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo

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

実験手順: To a stirred solution of (E)-3-cyclohexyl-2-propen-1-ol (A. G. M. Barrett et al, Tetrahedron, 1996, 52, 15325), (1.47 g, 10.5 mmol) in diethyl ether (20 ml) and pyridine (1 ml) was added phosphorus tribromide (1.40 ml, 15 mmol) dropwise at room temperature under an atmosphere of nitrogen. After 16 h, the reaction mixture was carefully poured onto ice water (100 ml) and extracted with diethyl ether (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by silica (20 g) column chromatography eluting with hexane:ethyl acetate (4:1) to give the title compound as a colourless oil (1.3 g, 61%). the reaction mixture was carefully poured onto ice water (100 ml) extracted with diethyl ether (100 ml) The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) dried (MgSO4) concentrated in vacuo to give the crude product This was purified by silica (20 g) column chromatography eluting with hexane:ethyl acetate (4:1)

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

実験手順: To a stirred solution of (E)-3-cyclohexyl-2-propen-1-ol (A. G. M. Barrett et al, Tetrahedron, 1996, 52, 15325), (1.47 g, 10.5 mmol) in diethyl ether (20 ml) and pyridine (1 ml) was added phosphorus tribromide (1.40 ml, 15 mmol) dropwise at room temperature under an atmosphere of nitrogen. Afler 16 h, the reaction mixture was carefully poured onto ice water (100 ml) and extracted with diethyl ether (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml), dried (MgSO4) and concentrated in vacuo to give the crude product. This was purified by silica (20 g) column chromatography cluting with hexane:ethyl acetate (4:1) to give the title compound as a colourless oil (1.3 g, 61%). Afler 16 h, the reaction mixture was carefully poured onto ice water (100 ml) extracted with diethyl ether (100 ml) The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) dried (MgSO4) concentrated in vacuo to give the crude product This was purified by silica (20 g) column chromatography