Octanal → HCID 86671848, compound

Participants

Reaction Steps

Octanal (385 mg, 469 μL, 3.0 mmol) was weighed into a 10 mL round bottom flask previously flushed with N2 and containing a stifling bar. To the flask was anhydrous Na2SO4 (4.26 g, 30 mmol), 6 mL of dry dichloromethane and finally, O-benzylhydroxylamine (369 mg, 349 μL, 3 mmol) over 2 min while maintaining positive N2 pressure. The reaction mixture was stirred overnight. The salt was filtered off and rinsed with dichloromethane. The combined filtrates and rinsings were concentrated. The crude material was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (95:5) to give 328 mg (47%) of a clear oil: Rf=0.45 and 0.51 (two isomers) (hexanes/ethyl acetate, 95:5, v/v); 1H NMR (CDCl3) δ 7.43 (t, 3J=6.3 Hz, 0.5H), 7.36-7.25 (m, 5H), 6.66 (t, 3J=5.5 Hz, 0.5H), 5.08 (s, 1H), 5.03 (s, 1H), 2.37-2.32 (m, 1H), 2.18-2.14 (m, 1H), 1.49-1.41 (m, 2H), 1.33-1.18 (m, 8H), and 0.86 (t, 3J=7 Hz, 3H). Exact mass (FAB+) calculated for C15H24NO [M+H] 234.1852. Found 234.1856.

Provenance & Evidence