[2-(Trifluoromethyl)pyridin-3-yl]methanol → 2-(Trifluoromethyl)pyridine-3-carbaldehyde
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[C:8]([CH2:9][OH:10])=[CH:7][CH:6]=[CH:5][N:4]=1>ClCCl.O=[Mn]=O>[F:11][C:2]([F:1])([F:12])[C:3]1[N:4]=[CH:5][CH:6]=[CH:7][C:8]=1[CH:9]=[O:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
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).
Workup
- filtrationAfter this time the mixture was filtered through Celite®
- concentrationthe filtrate concentrate in vacuo
- customto afford a brown oil
- customThis crude oil was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-749d22c014274c6688bcd73c5587a6e3
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150568B2
Reaction notes
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