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

HRID 841894Notes

Reaction equation

HRID 841894 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-52126947ad1443f1b6843443a67af49e
Source dataset
uspto-grants-2002_04
Patent number
US06372731B1

Reaction notes

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