[Al].II.[CH2:4](Br)[C:5]#[CH:6].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)[C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:11][CH:10]=1.[Cl-].[NH4+]>O1CCCC1.[Hg](Cl)Cl>[C:18]([C:17]([OH:22])([CH:16]([N:23]1[CH:27]=[N:26][CH:25]=[N:24]1)[CH2:15][C:12]1[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=1)[CH2:6][C:5]#[CH:4])([CH3:21])([CH3:20])[CH3:19]
3.7 g of aluminum (in the form of flakes), a pinch of mercury(II) chloride and an iodine crystal are stirred with 20 ml of absolute tetrahydrofuran for 12 hours. 24 g (0.2 mol) of propargyl bromide, dissolved in 25 ml of tetrahydrofuran, are then added dropwise at 50° to 60° C. The mixture is stirred for a further 30 minutes at 60° C. and cooled to -60° C., and 29.2 g (0.1 mol) of 5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-pentan-3-one in 100 ml of tetrahydrofuran are slowly added dropwise. Thereafter, the reaction mixture is stirred for a further hour at 0° C. and for 2 hours at 20° C., 50 ml of saturated, aqueous ammonium chloride solution are added, while cooling, the mixture is filtered and the filtrate is evaporated down. The remaining crystalline residue is digested with water and recrystallized from 520 ml of cyclohexane. 24.6 g (74.2% of theory) of 4-tert.-butyl-6-(4-chlorophenyl)-5-(1,2,4-triazol-1-yl)-hex-1-in-4-ol of melting point 121° C. are obtained.
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