Water → Diethyl 2-(7-octenyl)-2-(5,5,6,6,6-pentafluorohexyl)malonate

HRID 1267746Notes

Reaction equation

HRID 1267746 reaction equation
[H-].[Na+].[CH2:3]([CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].I[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29].O>CS(C)=O>[CH2:3]([C:11]([CH2:23][CH2:24][CH2:25][CH2:26][C:27]([F:32])([F:33])[C:28]([F:29])([F:30])[F:31])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 120170616-Iodo-1,1,1,2,2-pentafluorohexaneHCID 18546278Diethyl 2-(7-octenyl)malonate

Product 1

HCID 18546288Diethyl 2-(7-octenyl)-2-(5,5,6,6,6-pentafluorohexyl)malonateYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60%, 326 mg, 8.14 mmol) was added to dimethyl sulfoxide (5 ml) under argon atmosphere and cooled to 0° C. To this mixture, diethyl 2-(7-octeny)malonate (2 g, 7.40 mmol) dissolved in dimethyl sulfoxide (5 ml) was slowly added, followed by stirring for 1 hour. After cooling to 0° C., 1-iodo-5,5,6,6,6-pentafluorohexane (2.68 g, 8.88 mmol) dissolved in dimethyl sulfoxide (5 ml) was slowly added to the reaction mixture, followed by stirring for 2 hours at room temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20) to give diethyl 2-(7-octenyl)-2-(5,5,6,6,6-pentafluorohexyl)malonate (2.3 g, Yield 70%) as a colorless oil.

Workup

  1. additionwas slowly added
  2. temperatureAfter cooling to 0° C.
  3. additionwas slowly added to the reaction mixture
  4. stirringby stirring for 2 hours at room temperature
  5. extractionwas then extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationAfter distilling off the solvent
  9. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20)

Sources & evidence

ORD record
ord-cec4ba6d7c1d4e1196be05ea3876a4c7
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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