Water → HCID 57736351, compound

HRID 2261331Notes

Reaction equation

HRID 2261331 reaction equation
F[C:2](F)([C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH:3]=[C:4](I)[CH2:5][OH:6].[OH2:19].Cl.[NH2:21]O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:14][C:9]([F:15])([C:10]([F:13])([F:12])[F:11])[C:8]([F:17])([F:16])[C:2]1[O:19][N:21]=[C:4]([CH2:5][OH:6])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 86631047HCID 86631047, compound

Product 1

HCID 57736351HCID 57736351, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

14.94 g of 4,4,5,5,6,6,7,7,7-nonafluoro-2-iodo-2-heptene-1-ol was dissolved in 150 ml of ethanol, and 70 ml of water, 5.17 g of hydroxylamine hydrochloride and 25.67 g of potassium carbonate were then added. The mixture was stirred and heated under reflux for 24 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 3.53 g of (5-heptafluoropropyl-isoxazol-3-yl)methanol.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 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-608d1c8e3d7847f3bf2cdc3ddd200e19
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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