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

HRID 1789331Notes

Reaction equation

HRID 1789331 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

In 2,2,3,3-tetrafluoropropanol (10 ml) was dissolved 2,3-dimethyl-4-nitropyridine-1-oxide (2 g). To the solution was added potassium t-butoxide (1.6 g) little by little at room temperature. The mixture was then heated at 80°-90° C. for 22 hours. The reaction solution was diluted with water, which was subjected to extraction with chloroform. The extract was dried on magnesium sulfate, and then concentrated. The concentrate was chromatographed on a column of silica gel (70 g). Elution was conducted with methanol-chloroform (1:10), and then subjected to recrystallization from ethyl acetate-hexane to yield 2.6 g of 2,3-dimethyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine-1-oxide as colorless needles, m.p. 138°-139° C.

Workup

  1. temperatureThe mixture was then heated at 80°-90° C. for 22 hours
  2. extractionwas subjected to extraction with chloroform
  3. customThe extract was dried on magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was chromatographed on a column of silica gel (70 g)
  6. washElution
  7. customsubjected to recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f9d2463dc43f455aa100ca6eb792b428
Source dataset
uspto-grants-1987_08
Patent number
US04689333

Reaction notes

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