Water → 3-Oxo-2-(4,4,5,5,5-pentafluoropentyl)-dec-9-enoic acid ethyl ester

HRID 1792406Notes

Reaction equation

HRID 1792406 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6](=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[CH3:2].CC(C)([O-])C.[K+].[F:22][C:23]([F:32])([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:25][CH2:26]I.O>C1COCC1>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:26][CH2:25][CH2:24][C:23]([F:32])([F:22])[C:28]([F:31])([F:30])[F:29])[C:6](=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH2:13])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10036105Ethyl 3-oxo-9-decenoateHCID 120170571,1,1,2,2-Pentafluoro-5-iodopentaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 235380453-Oxo-2-(4,4,5,5,5-pentafluoropentyl)-dec-9-enoic acid ethyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

On the other hand, to a solution of 3-oxo-dec-9-enoic acid ethyl ester (4.32 g, 20.3 mmol) in THF (15 ml) at 0° C. was added potassium tert-butoxide (2.73 g, 24.3 mmol) This resulting mixture was stirred at room temperature under nitrogen for 30 min. The mixture of 4,4,5,5,5-pentafluoro-iodopentane was added and mixture was refluxed under nitrogen for 2 days, and then poured into H2O. The mixture was extracted with hexane. The organic layer was washed with saturated aqueous NaCl, dried over Na2SO4, filtered, concentrated, and purified by column chromatography (silica gel, 60% CHCl3/hexane) to afford 3-oxo-2-(4,4,5,5,5-pentafluoropentyl)-dec-9-enoic acid ethyl ester (4.46 g, 59%).

Workup

  1. additionwas added
  2. temperaturemixture was refluxed under nitrogen for 2 days
  3. extractionThe mixture was extracted with hexane
  4. washThe organic layer was washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography (silica gel, 60% CHCl3/hexane)

Sources & evidence

ORD record
ord-3a47379b3ceb4d8bb2427f79f266f219
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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