Triacetoxyperiodinane → 7-Oxo-azepane-2-carbaldehyde

Participants

Reaction Steps

750 mg of 7-hydroxymethyl-azepan-2-on (compound F1) are dissolved in 85 ml of dichloromethane under an atmosphere of dry nitrogen. Subsequently, 2.22 g of triacetoxy periodinane (Dess-Martin reagent) are added at room temperature and stirring is continued for further 3 hours. Thereafter, the suspension is evaporated to dryness to yield 2.65 g of crude material. The crude product is purified by chromatography (eluent gradient: cyclohexane/50-100 vol. % ethyl acetate) to afford 272 mg of the title compound as a colorless, waxy solid. ESI-MS: 140.1 (MH+). TLC: Rf=0.60 (dichloromethane/ethanol 10:1 parts by volume).

Provenance & Evidence