Water → Diethyl 2-(6-heptenyl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate

HRID 1267473Notes

Reaction equation

HRID 1267473 reaction equation
[F:1][C:2]([F:26])([C:16]([F:25])([F:24])[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])[CH2:3][CH2:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[H-].[Na+].I[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36].O>CS(C)=O>[CH2:36]([C:5]([CH2:4][CH2:3][C:2]([F:26])([F:1])[C:16]([F:24])([F:25])[C:17]([F:22])([F:23])[C:18]([F:21])([F:20])[F:19])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=[CH2:30]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 106328827-Iodohept-1-eneHCID 10916513Diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate

Product 1

HCID 18546295Diethyl 2-(6-heptenyl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonateYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-malonate prepared in Step 1 of Example 2 (1.2 g, 3.0 mmol) was slowly added dropwise to a suspension of 60% sodium hydride (288 mg, 12 mmol) in anhydrous dimethyl sulfoxide (20 ml) at 0° C., followed by stirring for 1 hour at room temperature. After 7-iodohept-1-ene (795 mg, 2.5 mmol) was slowly added dropwise, the reaction mixture was stirred for 12 hours at room temperature. Water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic layers were 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) to give diethyl 2-(6-heptenyl)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate (1.08 g, Yield 73%).

Workup

  1. stirringthe reaction mixture was stirred for 12 hours at room temperature
  2. extractionwas then extracted twice with ethyl acetate
  3. washThe combined organic layers were washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/40)

Sources & evidence

ORD record
ord-ed98654934404a2292ebd12e13421684
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

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