Water → 1-(3-Ethoxyphenyl)ethanone

HRID 353400Notes

Reaction equation

HRID 353400 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH2:11](I)[CH3:12].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.C(OCC)(=O)C>[CH2:11]([O:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1)[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 84873-HydroxyacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 37702501-(3-Ethoxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

3′-Hydroxyacetophenone (200 mg) was dissolved in acetonitrile (4 ml). After adding ethyl iodide (0.2 ml) and potassium carbonate (347 mg), the mixture was stirred at 70° C. for 9 hours. After 9 hours, water and ethyl acetate were added to the reaction mixture followed by separation. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered and concentrated. The crude product thus obtained was purified by silica gel chromatography (n-hexane:ethyl acetate=8:1) to thereby give 204 mg of 3′-ethoxyacetophenone. The procedure employed for the synthesis of F-12 was repeated but replacing the 3′-methoxyacetophenone by 3′-ethoxyacetophenone to thereby give (±)-N-(1-(3-ethoxyphenyl)ethyl)-2-(2′,5′-dichlorophenylthio)ethylamine (F-63). MS m/z: 369 (M+).

Workup

  1. waitAfter 9 hours
  2. customfollowed by separation
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product thus obtained
  8. customwas purified by silica gel chromatography (n-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-673cdcda02a74443a698a3228d6c9fa4
Source dataset
uspto-grants-2004_06
Patent number
US06750255B2

Reaction notes

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