Iodoethane → HCID 67071649, compound

HRID 2264011Notes

Reaction equation

HRID 2264011 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:13])([CH3:12])[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH:14](NC(C)C)(C)[CH3:15].C(I)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:14]([O:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:13])([CH3:12])[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1)[CH3:15]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 7912DiisopropylamineHCID 11430Potassium CarbonateHCID 67071651HCID 67071651, compound

Product 1

HCID 67071649HCID 67071649, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 3-(3-hydroxy-phenyl)-3-methyl-butan-2-one (3.4 g, 19.08 mmol), diisopropylamine (16.7 mL, 95.4 mmoL) and ethyl iodide (6.2 mL, 76.32 mmol) in 60 mL of ethanol was heated at refluxed overnight. Thin layer chromatography still showed starting material. Potassium carbonate (9 g) was added, and the mixture was heated at reflux for 12 h. It was concentrated in vacuo, and the residue was taken in ethyl acetate. After being washed with water and brine, the organic layer was dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated to give 3.727 g of 3-(3-ethoxy-phenyl)-3-methyl-butan-2-one as light brown oil. It was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat refluxed overnight
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 12 h
  5. concentrationIt was concentrated in vacuo
  6. washAfter being washed with water and brine
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. filtrationThe solids were filtered off
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-01bb9ebd2f65496a8a559f6e27da77e9
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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