Sodium Chloride → 1-[1-(1-Hydroxy-2,2,3,3,4,4,5,5,5-nonafluoropentyl)cyclopropyl]ethanone

HRID 842623Notes

Reaction equation

HRID 842623 reaction equation
[CH3:1][C:2]1([C:7]2([CH:10]([C:12]([F:24])([F:23])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[OH:11])[CH2:9][CH2:8]2)OCC[O:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl-].[Na+]>C(Cl)Cl.CO>[OH:11][CH:10]([C:7]1([C:2](=[O:3])[CH3:1])[CH2:9][CH2:8]1)[C:12]([F:23])([F:24])[C:13]([F:21])([F:22])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6101p-Toluenesulfonic acidHCID 226144181-(2-Methyl-1,3-dioxolan-2-yl)-alpha-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)cyclopropanemethanol

Product 1

HCID 226144071-[1-(1-Hydroxy-2,2,3,3,4,4,5,5,5-nonafluoropentyl)cyclopropyl]ethanoneYield 95.6%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

3.2 g of 98 in 50 ml of methylene chloride/methanol 1:1 is dissolved, and 750 mg of p-toluenesulfonic acid is added. It is stirred under argon for 2 hours at room temperature. Sodium chloride solution is added, extracted with methylene chloride, the organic phase is washed with sodium bicarbonate solution and sodium chloride-solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 2.7 g of 1-[1-(1-hydroxy-2,2,3,3,4,4,5,5,5-nonafluoropentyl)cyclopropyl]ethanone 99 is obtained as a colorless oil.

Workup

  1. extractionextracted with methylene chloride
  2. washthe organic phase is washed with sodium bicarbonate solution and sodium chloride-solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-94611229ae16484187f7ce564ff582f1
Source dataset
uspto-grants-2002_04
Patent number
US06376480B1

Reaction notes

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