Triacetoxyperiodinane → 4-(Trifluoromethyl)pyridine-2-carbaldehyde

Participants

Reaction Steps

To a solution of (4-trifluoromethyl-pyridin-2-yl)-methanol (290 mg, 1.64 mmol) in CH2Cl2 (15 mL) at room temperature was added Dess-Martin periodinane (764 mg, 1.8 mmol). The reaction mixture was stirred at room temperature for 1 h then quenched with saturated aqueous NaHCO3 (10 mL) and 10% aqueous Na2S2O3 (10 mL). The biphasic mixture was diluted with CH2Cl2 and stirred vigorously for 10 min. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organics were dried over MgSO4 and concentrated to give 300 mg of 4-trifluoromethyl-pyridine-2-carbaldehyde as a pale yellow oil which was used without further purification. 1H NMR (CDCl3, 300 MHz): δ (ppm) 10.15 (s, 1H), 9.00 (d, J=5.3 Hz, 1H), 8.19 (s, 1H), 7.77 (dd, J=5.3, 1.3 Hz, 1H).

Provenance & Evidence