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

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).

1. customthen quenched with saturated aqueous NaHCO3 (10 mL) and 10% aqueous Na2S2O3 (10 mL)
2. additionThe biphasic mixture was diluted with CH2Cl2
3. stirringstirred vigorously for 10 min
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with CH2Cl2
6. dry with materialThe combined organics were dried over MgSO4
7. concentrationconcentrated

ORD record

ord-41667316bf2d40b09166ede9ed673340

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658646B2