2,2,2-Trifluoroethanol → HCID 12056730, compound

HRID 50130Notes

Reaction equation

HRID 50130 reaction equation
N[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[F:8][C:9]([F:13])([F:12])[CH2:10][OH:11].FC(F)(F)C(O)=O.C(ON=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>>[F:8][C:9]([F:13])([F:12])[CH2:10][O:11][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 64092,2,2-TrifluoroethanolHCID 6422Trifluoroacetic acidHCID 100093-AminopyridineHCID 10906Tert-Butyl nitriteHCID 11430Potassium Carbonate

Product 1

HCID 12056730HCID 12056730, compoundYield 56.8%

Conditions

Temperature
15 °C

Procedure

A reactor vessel is charged with 3-aminopyridine (2.0 g, 21 mmol), 2,2,2-trifluoroethanol (15 g, 150 mmol), and trifluoroacetic acid (3.63 g, 31.8 mmol). The solution is cooled to 15° C. and then t-Butylnitrite (2.51 g of a 96% solution, 23.4 mmol) is added drop-wise to the vessel so that the temperature rises to the range 25° C.-30° C. Potassium carbonate (4.4 g) is added to the vessel and the reaction mass is stirred overnight followed by dilution with water and extraction with ethyl acetate. The solvent is evaporated to obtain 3-(2,2,2-trifluoroethoxy)pyridine as a crude oil (3.94 g, crude yield 59.5%) with an actual yield of 56.8%.

Workup

  1. customrises to the range 25° C.-30° C
  2. extractionfollowed by dilution with water and extraction with ethyl acetate
  3. customThe solvent is evaporated

Sources & evidence

ORD record
ord-9c2526ad1b3943308a5148cfd1fb78a7
Source dataset
uspto-grants-2004_03
Patent number
US06710180B2

Reaction notes

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