2,2,2-Trifluoroethanol → HCID 59570383, compound

HRID 623424Notes

Reaction equation

HRID 623424 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:12])([F:11])[CH2:9][OH:10].[N+]([C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]#[N:23])[CH:17]=1)([O-])=O.[Cl-].[NH4+]>O1CCCC1>[F:7][C:8]([F:12])([F:11])[CH2:9][O:10][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]#[N:23])[CH:17]=1

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 25517Ammonium ChlorideHCID 5686504-NitropicolinonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 59570383HCID 59570383, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium tert-butoxide (0.45 g, 4.02 mmol) in tetrahydrofuran (8 mL) is added 2,2,2-trifluoroethanol (0.27 mL, 3.69 mmol), and the mixture is stirred at room temperature for 20 minutes. A solution of 4-nitropicolinonitrile (0.50 g, 3.35 mmol) in tetrahydrofuran (8 mL) is added dropwise the mixture, and the resulting mixture is stirred at room temperature for 20 minutes. The reaction mixture is poured into saturated aqueous ammonium chloride solution (20 mL) and extracted with ethyl acetate (30 mL). The organic layer is dried over sodium sulfate and concentrated in vacuo to give 0.71 g (>99% yield) of the title compound as yellow oil. This material is used for the next reaction (Step-2) without further purification.

Workup

  1. stirringthe resulting mixture is stirred at room temperature for 20 minutes
  2. extractionextracted with ethyl acetate (30 mL)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3267f438e69448c89154f8f83c55b3de
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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