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A solution of vinyl magnesium chloride (2.2 Molar in tetrahydrofuran 35 mL) was added to tetrahydrofuran (150 mL) and cooled to -60°. The compound (E)-2-tridecen-4,7-diyn-1-al (12.6 g) dissolved in tetrahydrofuran (50 mL) was added to the above solution over 5-10 min and the cooling bath was removed and the temperature of the reaction mixture was allowed to warm to 0° C. (20 min). Ether (200 mL) was then added followed by a saturated aqueous solution of ammonium chloride (10 mL). After the contents of the flask had been stirred for a further 15 L min, magnesium sulfate was added and after a further 30 min, the solids were filtered off and washed with ether. Removal of the solvents from the combined filtrates and purification of the residue by liquid chromatography (two columns, 10% by volume ethyl acetate in 90% by volume hexane) yielded the pure (E)-1,4-pentadecadien-6,9-diyn-3-ol (13.2 g).

1. temperaturecooled to -60°
2. additionwas added to the above solution over 5-10 min
3. customthe cooling bath was removed
4. additionEther (200 mL) was then added
5. additionwas added and after a further 30 min
6. filtrationthe solids were filtered off
7. washwashed with ether
8. customRemoval of the solvents
9. customfrom the combined filtrates and purification of the residue by liquid chromatography (two columns, 10% by volume ethyl acetate in 90% by volume hexane)