2,2,2-Trifluoroethanol → 6-(2,2,2-Trifluoroethoxy)pyridine-3-carbonitrile

HRID 1436337Notes

Reaction equation

HRID 1436337 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[F:10][C:11]([F:15])([F:14])[CH2:12][OH:13].CC(C)([O-])C.[K+]>O>[F:10][C:11]([F:15])([F:14])[CH2:12][O:13][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 27771236-(2,2,2-Trifluoroethoxy)pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 6-chloronicotinonitrile (0.30 g, 2.2 mmol) was a mixture of 2,2,2-trifluoroethanol (0.19 mL, 2.6 mmol) and potassium tert-butoxide (1M solution in THF, 2.5 mL, 2.5 mmol) added at 0-5° C. The resulting mixture was stirred at ambient temperature for 1 hour. Water was added (20 mL) followed by extraction with ethyl acetate (2×20 mL). The organic layer was dried over sodium sulphate and concentrated in vacuum affording 6-(2,2,2-trifluoroethoxy)nicotinonitrile, 0.42 g (96%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.76 (d, J=2.26 Hz, 1 H) 8.28 (dd, J=8.53, 2.26 Hz, 1 H) 7.21 (d, J=8.78 Hz, 1 H) 5.09 (q, J=8.95 Hz, 2 H).

Workup

  1. additionadded at 0-5° C
  2. extractionfollowed by extraction with ethyl acetate (2×20 mL)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-7b28a4870e2848d58737192d18927b1e
Source dataset
uspto-grants-2009_11
Patent number
US07618993B2

Reaction notes

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