4-Oxo-1-iodo-trans-1-octene → 4-Hydroxy-4-(1-propynyl)-1-iodo-trans-1-octene

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Reaction Steps

To a stirred solution of propynyllithium at -25° is added a solution of 4-oxo-1-iodo-trans-1-octene in tetrahydrofuran. After the addition, the solution is stirred at -20° to -15° C. for 30 minutes. Tbe reaction is quenched with a mixture of hexane and ice. The aqueous phase is separated and extracted with additional hexane. The combined hexane extracts is washed successively with water and brine. The solution is dried over magnesium sulfate and concentrated. The residue is chromatographed on a silica gel column and is eluted with tolulene to provide the product as an oil.

Provenance & Evidence