[Li].N.C#CCCCC.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([O-:30])([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.[Li+]>CCOCC>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([OH:30])([C:24]#[C:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:23])=[CH:18][CH:17]=2)=[CH:14][CH:15]=18.34 g. of lithium is added at -70°, over three hours, to 900 ml. of liquid ammonia containing 82 g. of 1-hexyne. When the blue color has disappeared, 214 g. of 4'-fluoro-4-acetylbiphenylyl in 200 ml. of ether are added thereto over one hour. The solution contains lithium 2-(4'-fluoro-4-biphenylyl)-3-octyn-2-olate. Subsequently, the ammonia is allowed to evaporate at +25° and simultaneously ether is added at a rate such that the volume of the mixture remains constant. After removal of ammonia, the mixture is allowed to stand for 12 hours at 20°. Thereafter, it is hydrolyzed with 150 ml. water and worked up as usual, to give 2-(4'-fluoro-4-biphenylyl)-3-octyn-2-ol; m.p. 62°.
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