[CH3:1][C:2]([OH:10])([C:6]#[C:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5].[CH2:11]([Si:13](Cl)([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12].CN(C)C=O.C(N(CC)CC)C>O.C1C=CC=CC=1>[CH2:11]([Si:13]([O:10][C:2]([CH3:1])([C:6]#[C:7][CH2:8][CH3:9])[CH2:3][C:4]#[CH:5])([CH2:16][CH3:17])[CH2:14][CH3:15])[CH3:12]A mixture consisting of 1.25 parts of 4-methyl-1,5-octadiyn-4(RS)-ol, 1.5 parts of triethylsilyl chloride, 2.5 parts by volume of dimethylformamide and 1 part by volume of triethylamine was stirred in an atmosphere of nitrogen at room temperature for about 24 hours. The mixture was then poured into benzene and diluted with water. The layers were separated and the organic layer was washed successively with dilute hydrochloric acid, water and saturated aqueous potassium bicarbonate, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. Adsorption of the residue on a silica gel chromatographic column followed by elution with hexane afforded 4-methyl-1,5-octadiyn-4(RS)-ol triethylsilyl ether.
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