Triacetoxyperiodinane → 2-(1-Methoxycycloheptyl)-5-(trifluoromethyl)benzaldehyde

Participants

Reaction Steps

To a solution of (2-(1-methoxycycloheptyl)-5-(trifluoromethyl)phenyl)methanol (167 mg; 0.552 mmol) in methylene chloride (3.0 mL) was added Dess-Martin reagent (290 mg; 0.683 mmol). Reaction was stirred at room temperature for 5 hours. The reaction was diluted with ethyl acetate and quenched with aqueous 1N sodium hydroxide. After partitioning off the aqueous layer, the organic layer was washed with water and brine. It was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified over a Bakerbond 1 g silica cartridge (Mallinkrodt Baker Inc. Phillipsburg, N.J.) (eluted with 0-5% heptane) to yield 167 mg of a cloudy oil. 1H NMR (400 MHz, CDCl3) δ ppm 10.91 (s, 1H), 811 (d, J=2.07 Hz, 1H), 7.73 (dd, J=8.71, 8.30 Hz, 1H), 7.48 (d, J=7.88 Hz, 1H), 2.96 (s, 3H), 2.25 (m, 2H), 2.09 (m, 2H), 1.94-1.57 (m, 8H).

Provenance & Evidence