2,2,3,3-Tetrafluoro-1-propanol → HCID 13654791, compound

HRID 622155Notes

Reaction equation

HRID 622155 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N+:3]=1[O-:12].CC(C)([O-])C.[K+].[F:19][C:20]([F:26])([CH:23]([F:25])[F:24])[CH2:21][OH:22]>O>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([O:22][CH2:21][C:20]([F:26])([F:19])[CH:23]([F:25])[F:24])[CH:5]=[CH:4][N+:3]=1[O-:12]

Participants

5

Reactant 3

HCID 64412,2,3,3-Tetrafluoro-1-propanolHCID 1482232,3-Dimethyl-4-nitropyridine-N-oxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 13654791HCID 13654791, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,3-Dimethyl-4-nitropyridine-1-oxide (2 g) was dissolved in 2,2,3,3-tetrafluoropropanol (10 ml). To the resultant solution potassium t-butoxide (1.6 g) was added gradually at room temperature, after which the solution was heated at 80°~90° C. for 22 hours. The resulting reaction mixture was diluted with water, extracted with chloroform, dried over magnesium sulfate, concentrated, applied on silica gel (70 g) column, eluted with methanol-chloroform (1:10) and then recrystallized from ethyl acetate-hexane to give 2.6 g of 2,3-dimethyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine-1-oxide as color less needles (melting point: 138°~139° C.).

Workup

  1. temperatureafter which the solution was heated at 80°~90° C. for 22 hours
  2. customThe resulting reaction mixture
  3. extractionextracted with chloroform
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with methanol-chloroform (1:10)
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-901006da230f42ccaf226b169c8c6d72
Source dataset
uspto-grants-1988_09
Patent number
US04769456

Reaction notes

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