2-Chloro-3-(trifluoromethyl)pyridine → 2-Ethoxy-3-(trifluoromethyl)pyridine

HRID 906829Notes

Reaction equation

HRID 906829 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[O-:12][CH2:13][CH3:14].[Na+]>C(O)C>[CH2:13]([O:12][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:14]

Participants

4

Reactant 2

HCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 2723922Sodium ethoxide

Product 1

HCID 426323562-Ethoxy-3-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-3-trifluoromethyl-pyridine (4.43 g, 24.4 mmol) was dissolved in 42 ml 21% (wt.) sodium ethoxide in ethanol. The mixture was stirred at ambient temperature for 1.5 days. After this period of time, the solvent was evaporated and the residue was taken into water and extracted with dichloromethane three times. The combined extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo to give 2-ethoxy-3-trifluoromethyl-pyridine as a light liquid (3.42 g, 73% yield). The crude product was used directly for the next step. 1H-NMR (400 MHz, CDCl3): δ 1.42 (t, 3H, J=7.07), 4.49 (q, 2H, J=7.07), 6.94 (dd, 1H, J=7.45, J=5.05), 7.85 (dd, 1H, J=1.26, J=7.45), 8.30 (dd, 1H, J=1.26, J=5.06).

Workup

  1. waitAfter this period of time
  2. customthe solvent was evaporated
  3. extractionextracted with dichloromethane three times
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-220892ab19bd48f289505201640acd37
Source dataset
uspto-grants-2011_09
Patent number
US08013001B2

Reaction notes

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