Water → Diethyl 2-(5-hexenyl)-2-(4,4,5,5,5-pentafluoropentyl)malonate

HRID 460449Notes

Reaction equation

HRID 460449 reaction equation
[F:1][C:2]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:3][CH2:4][CH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30].O>CS(C)=O>[CH2:30]([C:6]([CH2:5][CH2:4][CH2:3][C:2]([F:21])([F:1])[C:17]([F:18])([F:19])[F:20])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:29][CH2:28][CH2:27][CH:26]=[CH2:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 759066-Bromo-1-hexeneHCID 12017062Diethyl 2-(4,4,5,5,5-pentafluoropentyl)malonate

Product 1

HCID 22718044Diethyl 2-(5-hexenyl)-2-(4,4,5,5,5-pentafluoropentyl)malonateYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of diethyl 2-(4,4,5,5,5-pentafluoropentyl)malonate (4.0 g, 12.5 mmol) in dimethyl sulfoxide (30 ml) was cooled to 10° C. To this solution, 60% sodium hydride (600 mg, 15 mmol) was added, and the resulting mixture was stirred for 1 hour at room temperature. 6-Bromo-1-hexene (2.5 ml, 18.75 mmol) was slowly added dropwise to the reaction mixture, followed by stirring for 3 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 saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/9) to give diethyl 2-(5-hexenyl)-2-(4,4,5,5,5-pentafluoropentyl)malonate (3.86 g, Yield 77%).

Workup

  1. stirringby stirring for 3 hours at room temperature
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/9)

Sources & evidence

ORD record
ord-6856c55159b6453791ce1b2bfe3d750e
Source dataset
uspto-grants-2007_03
Patent number
US07196081B2

Reaction notes

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