Isobutyl iodide → HCID 22678119, compound

HRID 1837552Notes

Reaction equation

HRID 1837552 reaction equation
I[CH2:2][CH:3]([CH3:5])[CH3:4].[C:6]([C:9]1[CH:18]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[C:12]([OH:19])=[CH:11][CH:10]=1)(=[O:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:6]([C:9]1[CH:10]=[CH:11][C:12]([O:19][CH2:2][CH:3]([CH3:5])[CH3:4])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 10556Isobutyl iodide3×HCID 11430Potassium Carbonate3×HCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 22678119HCID 22678119, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

1-Iodo-2-methylpropane (13.35 ml, 117 mmol) was added to a mixture of methyl 5-acetylsalicylate (15 g, 77 mmol) and potassium carbonate (16 g, 117 mmol) in acetonitrile (500 ml), and the reaction stirred at 60° C. for 18 hours. TLC analysis showed starting material remaining, so additional 1-iodo-2-methylpropane (26.7 ml, 234 mmol) and potassium carbonate (16 g, 117 mmol) were added and the reaction stirred at 60° C. for a further 72 hours. TLC analysis showed starting material still remaining, so additional 1-iodo-2-methylpropane (13.35 ml, 117 mmol) and potassium carbonate (16 g, 117 mmol) were added and the reaction stirred at reflux for a further 3 hours. The cooled mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and 1N sodium hydroxide solution. The phases were separated, the aqueous extracted with further ethyl acetate, and the combined organic solutions washed with brine, dried (MgSO4) and evaporated under reduced pressure to give the title compound as a brown oil, 8.3 g.

Workup

  1. stirringthe reaction stirred at 60° C. for a further 72 hours
  2. stirringthe reaction stirred
  3. temperatureat reflux for a further 3 hours
  4. concentrationThe cooled mixture was concentrated under reduced pressure
  5. customthe residue partitioned between ethyl acetate and 1N sodium hydroxide solution
  6. customThe phases were separated
  7. extractionthe aqueous extracted with further ethyl acetate
  8. washthe combined organic solutions washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-99c360bc0d844501ba43b25b7c4b1b2a
Source dataset
uspto-grants-2004_08
Patent number
US06784185B2

Reaction notes

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