Iodoethane → 2-Pent-2-ynyloxy-tetrahydro-pyran

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Reaction Steps

THF (2 ml) is added to 68 mg of sodium hydride (content: 47%), and 293 mg of ethyl iodide and 100 mg of the propargyl tetrahydropyranyl ether obtained as above is added to the mixture. The resulting mixture is refluxed for 12 hours and then cooled to room temperature. Several droplets of water are added to the mixture. After the evolution of hydrogen gas has ceased, one ml of 10% aqueous solution of ammonium chloride is added to the reaction mixture, and the mixture is then extracted with ether. The solvent is distilled off, and the residue is further distilled in a vacuum, giving 2-pentynyl tetrahydropyranyl ether, the desired product. The yield resulting from purification by column chromatography (SiO2) is 94%, b.p. 110°-113° C./17 mm Hg. (In the following examples, the product will be purified similarly.)

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