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Starting with 5-hexen-2-one, a Grignard reaction was carried out with ethynyl magnesium bromide in tetrahydrofuran (THF) solution to introduce an alkynyl group via nucleophilic addition, followed by acidic hydrolysis to obtain 3-methyl-6-hepten-1-yn-3-ol.

[1] SHAZIA ANJUM   José M C. PtCl2-mediated cycloisomerization of unsaturated propargylic carboxylates[J]. Tetrahedron, 2005, 61 20: Pages 4793-4803. DOI:10.1016/j.tet.2005.03.019.