C([Mg]Br)C.[CH3:5][CH:6]([CH2:9][CH3:10])[C:7]#[CH:8].[CH3:11][C:12]([CH3:22])([C:14](=[O:21])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[CH3:13].[Cl-].[NH4+]>C(OCC)C.ClCCl>[CH3:13][C:12]([CH3:22])([C:14]([OH:21])([C:8]#[C:7][CH:6]([CH3:5])[CH2:9][CH3:10])[CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[CH3:11]10 To a solution of ethyl magnesium bromide (20 ml) of a 3M solution in diethyl ether) in dry diethyl ether (30 ml) under N2 at room temperature was added a solution of 3-methyl-1-pentyne (5 g, 0.06 mol) in diethyl ether (20 ml). The resulting mixture was heated under reflux for 1 hour, and then cooled to 0° C. To this mixture was added slowly a solution of 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butane-3-one (8.4 g, 0.05 mol) in dry dichloromethane (150 ml), and the mixture stirred for 45 minutes, a gelatinous precipitate formed. Ammonium chloride solution was added to the mixture, and the organic layer separated and washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica eluting with diethyl ether (20-100%) in petrol gave 2,2-dimethyl-3-hydroxy-3-(3-methyl-pent-1-yne-1-yl)-4-(1,2,4-triazol-1-yl)-butane) as a white solid (4.29 g) (mpt=59°-60° C.).
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