Hydrochloric Acid → Uniconazole

Participants

Reaction Steps

To a solution of 1.08 g (0.0284 mole) of LiAlH4 in 85 cc of ethyl ether, while being cooled in ice, was added dropwise 22 cc of an ether solution containing 6.86 g (0.0284 mole) of (+)-2-N-benzyl-N-methylamino-1-phenylethanol followed by 40 cc of an ether solution containing 6.90 g (0.0564 mole) of N-ethylaniline. After having been stirred at room temperature for 3 hours, the mixture was cooled to -78° C. To the mixture was added dropwise 55 cc of an ether solution containing 2.75 g (0.0095 mole) of (E)-1-(4-chlorphenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-one. The mixture was stirred at said temperature for 3 hours and left standing overnight at room temperature. To the mixture was then added 105 cc of 2 N hydrochloric acid to effect decomposition. The organic layer was separated, washed successively with 100 cc of a saturated aqueous sodium hydrogencarbonate solution and 100 cc of ice-cooled water, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2.83 g of a crude product: [α]D24 -6.44 (c=1.05, CHCl3). A 2.8 g portion of the crude product was recrystallized three times from a cyclohexane-methanol mixture to obtain 0.82 g of (-)-(E)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)-4,4-dimethyl-1-penten-3-ol: [α]D24 -14.9 (c=1.0, CHCl3).

Provenance & Evidence