Synthesis of acetylenic diols

Abstract
Lithium naphthalene reacts with acetylenic carbinol, such as 3-methyl-1-butyn-3-ol or propargyl alcohol, to give the corresponding dilithio compounds. The reaction of these dilithio compounds with various ketones gives the corresponding acetylenic diols in good yield. By the new convenient one-step procedure for chain-lengthening, various acetylenic diols can be prepared from two kinds of ketones and acetylene using lithium naphthalene.

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