C(N)C.Cl.NO.[CH2:7]([OH:10])[C:8]#[CH:9].Br[C:12]#[C:13][C:14]([O:17][CH3:18])([CH3:16])[CH3:15]>CO.[Cu]Cl>[CH3:18][O:17][C:14]([CH3:16])([CH3:15])[C:13]#[C:12][C:9]#[C:8][CH2:7][OH:10]
200 ml of a 70% aqueous solution of ethyamine, 1 g of copper(I) chloride, 5 g of hydroxylamine hydrochloride and 25 g of propargyl alcohol were dissolved in 500 ml of methanol, and with ice cooling and stirring, a methanol solution (100 ml) of 74 g of 1-bromo-3-methoxy-3-methyl-1-butyne was added. The mixture was stirred at room temperature for 1 hour, and then the solvent was evaporated. Water and ethyl acetate were added, and the insoluble material was removed by filtration. The organic layer separated was worked up in a customary manner, and the product was purified by vacuum distillation ( b.p. -97° C. / 2 mmHg ) to give 57 g of the captioned compound as a colorless oil.
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