2,2,2-Trifluoroethanol → HCID 67509377, compound

HRID 715358Notes

Reaction equation

HRID 715358 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:12])([F:11])[CH2:9][OH:10].Cl[C:14]1[N:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][C:15]=1[O:23][CH3:24].[Cl-].[NH4+]>C1COCC1>[CH3:24][O:23][C:15]1[CH:16]=[C:17]([C:20](=[O:22])[CH3:21])[CH:18]=[N:19][C:14]=1[O:10][CH2:9][C:8]([F:12])([F:11])[F:7]

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 87426205HCID 87426205, compound

Product 1

HCID 67509377HCID 67509377, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium tert-butoxide (0.22 g, 1.97 mmol) in THF (7 mL) is added 2,2,2-trifluoroethanol (0.09 mL, 1.28 mmol), and the mixture is stirred at rt for 20 minutes. A solution of 1-(6-chloro-5-methoxypyridin-3-yl)ethanone (0.18 g, 0.99 mmol, Step-2) in THF (8 mL) is added dropwise to the mixture, and the resulting mixture is stirred at rt for 3.5 hours. The reaction mixture is poured into saturated aqueous ammonium chloride solution (20 mL) and extracted with EtOAc (30 mL). The organic layer is dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (4:1) to give 0.25 g (>99% yield) of the title compound as white solid.

Workup

  1. stirringthe resulting mixture is stirred at rt for 3.5 hours
  2. extractionextracted with EtOAc (30 mL)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (4:1)

Sources & evidence

ORD record
ord-14b60408a8e14be29f53e3645a8178aa
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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