Water → HCID 57736340, compound

HRID 2261329Notes

Reaction equation

HRID 2261329 reaction equation
F[C:2](F)([C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[CH:3]=[C:4](I)[CH2:5][OH:6].[OH2:16].Cl.[NH2:18]O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:13][C:8]([F:14])([C:2]1[O:16][N:18]=[C:4]([CH2:5][OH:6])[CH:3]=1)[C:9]([F:12])([F:11])[F:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 6145864,4,5,5,6,6,6-Heptafluoro-2-iodo-2-hexen-1-ol

Product 1

HCID 57736340HCID 57736340, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.9 g of 4,4,5,5,6,6,6-heptafluoro-2-iodo-2-hexene-1-ol was dissolved in 90 ml of ethanol, and 40 ml of water, 4.17 g of hydroxylamine hydrochloride and 20.70 g of potassium carbonate were then added. The mixture was stirred and heated under reflux for 20 hours. The reaction mixture was concentrated under reduced pressure. After water was added, the residue was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.78 g of (5-pentafluoroethyl-isoxazol-3-yl)methanol.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionAfter water was added
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27162c532c454ace84b871cc296cc441
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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