ethyl 4-iodocyclohexane-1-carboxylate

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

実験手順: To a cold (0° C.) stirred solution of 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (1.0 g, 5.80 mmol) in 1:2 CH2Cl2/CCl4 (52 ml) is added triphenylphosphine (1.82 g, 6.96 mmol), imidazole (473 mg, 6.96 mmol), and iodine (1.79 g, 7.08 mmol). The reaction is allowed to warm to room temperature and stirred overnight. The reaction is quenched by the addition of saturated sodium thiosulphate (c.a. 50 ml) and stirred until the solution becomes clear. The layers are separated and the aqueous layer is extracted with CH2Cl2 (3×30 ml). The combined organic phases are washed with sodium thiosulphate (30 ml), brine (30 ml), dried with anhydrous MgSO4, filtered and evaporated at reduced pressure to an oily solid. Purification by dry flash chromatography, Keiselgel 15-40 grade silica, eluting with 3% ethyl acetate/iso hexane yields the title compound as a clear colourless oil. The reaction is quenched by the addition of saturated sodium thiosulphate (c.a. 50 ml) stirred until the solution The layers are separated the aqueous layer is extracted with CH2Cl2 (3×30 ml) The combined organic phases are washed with sodium thiosulphate (30 ml), brine (30 ml) dried with anhydrous MgSO4 filtered evaporated at reduced pressure to an oily solid Purification by dry flash chromatography, Keiselgel 15-40 grade silica eluting with 3% ethyl acetate/iso hexane

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

実験手順: To a cold (0° C.) stirred solution of 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (1.0 g, 5.80 mmol) in 1:2 CH2Cl2/CCl4 (52 ml) is added triphenylphosphine (1.82 g, 6.96 mmol), imidazole (473 mg, 6.96 mmol), and iodine (1.79 g, 7.08 mmol). The reaction is allowed to warm to room temperature and stirred overnight. The reaction is quenched by the addition of saturated sodium thiosulphate (c.a. 50 ml) and stirred until the solution becomes clear. The layers are separated and the aqueous layer is extracted with CH2Cl2 (3×30 ml). The combined organic phases are washed with sodium thiosulphate (30 ml), brine (30 ml), dried with anhydrous MgSO4, filtered and evaporated at reduced pressure to an oily solid. Purification by dry flash chromatography, Keiselgel 15-40 grade silica, eluting with 3% ethyl acetate/iso hexane yields the title compound as a clear colourless oil. The reaction is quenched by the addition of saturated sodium thiosulphate (c.a. 50 ml) stirred until the solution The layers are separated the aqueous layer is extracted with CH2Cl2 (3×30 ml) The combined organic phases are washed with sodium thiosulphate (30 ml), brine (30 ml) dried with anhydrous MgSO4 filtered evaporated at reduced pressure to an oily solid Purification by dry flash chromatography, Keiselgel 15-40 grade silica eluting with 3% ethyl acetate/iso hexane

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

実験手順: To a cold (0° C.) stirred solution of 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (1.0 g, 5.80 mmol) in 1:2 CH2Cl2/CCl4 (52 ml) is added triphenylphosphine (1.82 g, 6.96 mmol), imidazole (473 mg, 6.96 mmol), and iodine (1.79 g, 7.08 mmol). The reaction is allowed to warm to room temperature and stirred overnight. The reaction is quenched by the addition of saturated sodium thiosulphate (c.a. 50 ml) and stirred until the solution becomes clear. The layers are separated and the aqueous layer is extracted with CH2Cl2 (3×30 ml). The combined organic phases are washed with sodium thiosulphate (30 ml), brine (30 ml), dried with anhydrous MgSO4, filtered and evaporated at reduced pressure to an oily solid. Purification by dry flash chromatography, Keiselgel 15-40 grade silica, eluting with 3% ethyl acetate/iso hexane yields the title compound as a clear colourless oil. The reaction is quenched by the addition of saturated sodium thiosulphate (c.a. 50 ml) stirred until the solution The layers are separated the aqueous layer is extracted with CH2Cl2 (3×30 ml) The combined organic phases are washed with sodium thiosulphate (30 ml), brine (30 ml) dried with anhydrous MgSO4 filtered evaporated at reduced pressure to an oily solid Purification by dry flash chromatography, Keiselgel 15-40 grade silica eluting with 3% ethyl acetate/iso hexane