Diethyl Malonate → Diethyl 2-(4,4,5,5,5-pentafluoropentyl)malonate

HRID 1792352Notes

Reaction equation

HRID 1792352 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:14][C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[CH2:17][CH2:18][CH2:19]I>O1CCCC1>[F:21][C:16]([F:22])([C:15]([F:24])([F:23])[F:14])[CH2:17][CH2:18][CH2:19][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 120170571,1,1,2,2-Pentafluoro-5-iodopentane

Product 1

HCID 12017062Diethyl 2-(4,4,5,5,5-pentafluoropentyl)malonateYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium hydride (60%) (3.90 g, 96.07 mol) in tetrahydrofuran (160 ml) was added dropwise a solution of diethyl malonate (16.6 ml, 110.85 mol) under ice-cooling, which was then stirred for 30 minutes. Then, 1,1,1,2,2-Pentafluoro-5-iodopentane (21 g, 73.9 mol) was added dropwise thereto, and reaction mixture was warmed to room temperature, with stirring, for overnight. After the reaction was completed, the reaction was quenched with water, extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and removed by evaporation under reduced pressure. This product was purified by column chromatography on silica gel, eluting with dichloromethane:n-hexane=1:3 to afford 18.3 g of the title compound as a colorless oil. (yield: 78.4%)

Workup

  1. temperaturecooling
  2. customreaction mixture
  3. stirringwith stirring, for overnight
  4. customthe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customremoved by evaporation under reduced pressure
  9. customThis product was purified by column chromatography on silica gel
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-68567e9f77644b129cad0d4e13d30b5f
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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