Trimethylamine oxide → 2,2-Dimethyl-6-oxohexanenitrile

Participants

Reaction Steps

To a suspension of trimethylamine oxide (1.5 g, 19.6 mmol, Aldrich) in DMSO (10 mL) was added 6-bromo-2,2-dimethylhexanenitrile (0.84 mL, 4.9 mmol, Aldrich). After stirring at room temperature overnight, the reaction mixture was quenched with water (10 mL) and extracted with hexanes (4×10 mL). The combined organic extracts were washed with brine (20 mL), dried (NaSO4), filtered and concentrated to afford 0.65 g (80% pure) of the title compound. MS (ESI+) m/z 157 (M+NH4)+.

Provenance & Evidence