Water → Ethyl 2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)-8-nonenoate

HRID 1267476Notes

Reaction equation

HRID 1267476 reaction equation
[Cl-].[Li+].O.[CH2:4]([C:11]([CH2:22][CH2:23][CH2:24][C:25]([F:37])([F:36])[C:26]([F:35])([F:34])[C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])(C(OCC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10]>CS(C)=O>[F:36][C:25]([F:37])([C:26]([F:34])([F:35])[C:27]([F:32])([F:33])[C:28]([F:29])([F:31])[F:30])[CH2:24][CH2:23][CH2:22][CH:11]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 962Water2×HCID 433294Lithium ChlorideHCID 12015792HCID 12015792, compound

Product 1

HCID 12015793Ethyl 2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)-8-nonenoateYield 44.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Lithium chloride (985 mg, 23.24 mmol) and water (0.21 ml, 11.62 mmol) were added to a solution of diethyl 2-(6-heptenyl)-2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)malonate (6.0 g, 11.62 mmol) in dimethyl sulfoxide (40 ml) followed by stirring for 12 hours at a temperature of 160° C. to 180° C. After the reaction was completed, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/40→1/30) to give ethyl 2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)-8-nonenoate (2.3 g, Yield 44%) as a colorless oil.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/40→1/30)

Sources & evidence

ORD record
ord-243dbade53b249d4b59f8320efdaef46
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

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