p-Toluenesulfonic acid → HCID 21521689, compound

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Reaction Steps

Typically, 1-octyn-3-ol is allowed to react with dihydropyran in the presence of a catalytic amount of p-toluenesulfonic acid to form the 3-pyranyl ether. 3-(tetrahydropyran-2-yl)oxy-1-octyne. That material is treated with diisobutyl aluminum hydride, then with iodine, to yield the corresponding iodo-octene, 3-(tetrahydropyran- 2-yl)oxy-1-iodo-1-octene. Magnesium metal, activated with mercuric chloride, is added to the iodo-octene and that addition is followed by the addition of cuprous iodide to yield 3-(tetrahydropyran-2-yl)oxy-trans-1-octenyl copper.

Provenance & Evidence