HCID 67272592, compound → 3-Methyl-5-(trifluoromethyl)pyridine-2-carbaldehyde

HRID 250948Notes

Reaction equation

HRID 250948 reaction equation
C[C:2]1([CH2:13][OH:14])[C:7]([CH3:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][NH:3]1>C(Cl)Cl.O=[Mn]=O>[CH3:8][C:7]1[C:2]([CH:13]=[O:14])=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:10])[F:11])[CH:6]=1

Participants

4

Reactant 1

HCID 67272592HCID 67272592, compound

Product 1

HCID 716270703-Methyl-5-(trifluoromethyl)pyridine-2-carbaldehydeYield 61%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of (2,3-dimethyl-5-trifluoromethyl-pyridin-2-yl)-methanol (0.300 g, 1.57 mmol)) and activated MnO2 (1.36 g, 15.6 mmol) in CH2Cl2 (10 mL) was stirred at room temperature overnight. After that period of time the suspension was filtered through a celite cake. the solvent was removed from the filtrate, and the residue was purified on silica gel column (CH2Cl2) to afford 3-methyl-5-trifluoromethyl-pyridine-2-carbaldehyde as a pale yellow liquid (0.180 g, 61%). 1H NMR (CD3Cl) δ 2.73 (s, 3H), 7.87 (s, 1H), 8.90 (s, 1H), 10.23 (s, 1H).

Workup

  1. filtrationAfter that period of time the suspension was filtered through a celite cake
  2. customthe solvent was removed from the filtrate
  3. customthe residue was purified on silica gel column (CH2Cl2)

Sources & evidence

ORD record
ord-e58ed3d57f9a43e4ae04bdc1886a1d21
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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