[2-(Trifluoromethyl)pyridin-3-yl]methanol → 2-(Trifluoromethyl)pyridine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

MnO2 (6.10 g, 70.6 mmol) was added portionwise to a solution of the above (2-(trifluoromethyl)pyridin-3-yl)methanol (I-29A) (2.5 g, 14.1 mmol) in dry dichloromethane (300 mL), and the resulting suspension was heated to 50° C. for 72 hours. After this time the mixture was filtered through Celite® and the filtrate concentrate in vacuo to afford a brown oil. This crude oil was purified by silica gel chromatography using a gradient of 0-30% ethyl acetate-hexane to furnish 2-(trifluoromethyl)nicotinaldehyde (I-29B) as clear oil. 1H-NMR (400 MHz, CDCl3) δ 10.4 (m, 1H), 8.89 (dd, J=4.8 and 1.2 Hz, 1H), 8.45 (dd, J=8.0, and 1.6 Hz, 1H), 7.70 (dd, J=8.0 and 4.8 Hz, 1H). MS m/z 176.0 (M+1).

Provenance & Evidence