Water → HCID 12015792, compound

HRID 1267475Notes

Reaction equation

HRID 1267475 reaction equation
[H-].[Na+].[CH2:3]([CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].I[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].O>O1CCCC1>[CH2:3]([C:10]([CH2:22][CH2:23][CH2:24][C:25]([F:36])([F:37])[C:26]([F:34])([F:35])[C:27]([F:32])([F:33])[C:28]([F:29])([F:31])[F:30])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 120167744,4,5,5,6,6,7,7,7-Nonafluoroheptyl iodideHCID 18546274Diethyl 2-(6-heptenyl)malonate

Product 1

HCID 12015792HCID 12015792, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% sodium hydride (0.54 g, 13.5 mmol) was added to a solution of diethyl 2-(6-heptenyl)malonate (3.0 g, 11.7 mmol) in tetrahydrofuran (30 ml) followed by stirring for 30 minutes at room temperature. 1-Iodo-4,4,5,5,6,6,7,7,7-nonafluoroheptane (5.45 g, 14.04 mmol) was added to the mixture followed by stirring for 12 hours at room temperature. 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=1/25) to give diethyl 2-(6-heptenyl)-2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)malonate (6.14 g, quantitative) as a colorless oil.

Workup

  1. stirringby stirring for 12 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 magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/25)

Sources & evidence

ORD record
ord-0726abbee2f64c1fbc4ef560641d4557
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

Loading…