6-(prop-2-yn-1-yloxy)hexan-1-ol

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

实验步骤: 118 g. of 1,6-hexanediol are introduced into 800 ml. of absolute tetrahydrofuran and, while stirring well, treated portionwise over a period of 4 hours with 30 g. of sodium hydride. 60 ml. of hexamethylphosphoric acid triamide are then added, the mixture is heated to reflux and treated over a period of 12 hours with a solution of 149 g. of propargyl bromide and 200 ml. of tetrahydrofuran. The cooled mixture is poured on to ice-water and extracted three times with ether. The ether solutions are washed with water and sodium chloride solution, dried over sodium sulphate and evaporated. By distillation or chromatography there is obtained pure 6-(2-propynyloxy)-1-hexanol; boiling point (bulb-tube) = 75°C/0.015 mmHg; nD25 = 1.4560. treated portionwise over a period of 4 hours with 30 g the mixture is heated to reflux treated over a period of 12 hours with a solution of 149 g extracted three times with ether The ether solutions are washed with water and sodium chloride solution dried over sodium sulphate evaporated By distillation or chromatography

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

实验步骤: A mixture of 1-(4-iodophenyl)piperidine (1.5 g), 6-[(2-propynyl)oxy]-1-hexanol (820 mg), BTPC (35 mg) and copper (I) iodide (20 mg) in diethylamine (30 ml) under nitrogen, was stired at room temperature overnight. The solvent was evaporated and the residue was partitioned between EA (50 ml) and 8% aqueous sodium bicarbonate (50 ml). The organic layer was washed with water and brine, dried and concentrated to a dark oil which was purified by FCC eluting with ER to give the title compound as an orange oil (1.2 g), t.l.c. (ER) Rf 0.70. The solvent was evaporated the residue was partitioned between EA (50 ml) and 8% aqueous sodium bicarbonate (50 ml) The organic layer was washed with water and brine dried concentrated to a dark oil which was purified by FCC eluting with ER