[CH:1](=[N:3]/[OH:4])\[CH3:2].[CH3:5][C:6]([NH2:10])([C:8]#[CH:9])[CH3:7].C(N(CC)CC)C.Cl[O-].[Na+]>C(Cl)Cl>[CH3:5][C:6]([NH2:10])([C:8]1[O:4][N:3]=[C:1]([CH3:2])[CH:9]=1)[CH3:7]
To a solution of (E)-acetaldehyde oxime (CAN 107-29-9, 1.0 g, 16.9 mmol), 2-methylbut-3-yn-2-amine (CAN 2978-58-7, 1.4 g, 16.9 mmol) and triethylamine (CAN 121-44-8, 0.17 g, 1.69 mmol) in methylene chloride (25 mL) at 0° C. was added a 5% aqueous solution of sodium hypochlorite (5%, 42.6 g) over 3 h. The reaction was allowed to warm to 4° C. and stirring continued for 5 h. The organic layer was separated, and the aqueous layer was extracted with methylene chloride (50 mL). The combined methylene chloride extracts were washed with saturated aqueous sodium chloride (60 mL) and dried over anhydrous magnesium sulfate. The solvent was removed to give a yellow oil. The crude product was purified by column chromatography (silica gel 30 g, eluting with 30% ethyl acetate in petroleum ether) to yield the product as yellow solid (0.1 g, 4.2%); MS (EI): m/e=141.2 [M+H]+.
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