1-Iodohexane → Ethyl 2-Hexylhexan-3-onecarboxylate

HRID 1698848Notes

Reaction equation

HRID 1698848 reaction equation
[Na].[CH2:2]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3][C:4](=[O:8])[CH2:5][CH2:6][CH3:7].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)C>[CH2:15]([CH:3]([C:4](=[O:8])[CH2:5][CH2:6][CH3:7])[CH2:2][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 125271-IodohexaneHCID 5360545SodiumHCID 12271529Ethyl 4-oxoheptanoate

Product 1

HCID 18322309Ethyl 2-Hexylhexan-3-onecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under an atmosphere of argon, 1.59 g (69.3 mmol) of sodium were added a little at a time to 50 ml of ethanol. The mixture was then stirred under reflux until a homogeneous solution was obtained. 11.0 g (69.3 mmol) of ethyl hexan-3-onecarboxylate were added to the hot alkoxide solution, and the mixture was stirred for 45 min. 6.51 ml (7.93 g, 52.5 mmol) of 1-iodohexane were then slowly added dropwise to the boiling mixture. The mixture was stirred under reflux for 16 h, cooled to room temperature and filtered, and the solvent was then removed under reduced pressure. The residue was taken up in dichloromethane, filtered again and concentrated. The crude product was purified chromatographically (silica gel, petroleum ether: ethyl acetate 30:1). MS (DCI, NH3): 309 [M+H]+.

Workup

  1. temperatureunder reflux until a homogeneous solution
  2. customwas obtained
  3. stirringthe mixture was stirred for 45 min
  4. stirringThe mixture was stirred
  5. temperatureunder reflux for 16 h
  6. filtrationfiltered
  7. customthe solvent was then removed under reduced pressure
  8. filtrationfiltered again
  9. concentrationconcentrated
  10. customThe crude product was purified chromatographically (silica gel, petroleum ether: ethyl acetate 30:1)

Sources & evidence

ORD record
ord-87c4977085664f4eb1367e5b4ca68c2a
Source dataset
uspto-grants-2002_02
Patent number
US06344471B1

Reaction notes

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