Sulfoxonium, trimethyl-, iodide (1:1) → HCID 21931845, compound

HRID 1243991Notes

Reaction equation

HRID 1243991 reaction equation
[I-].C[S+](C)(C)=O.[CH2:7]([Li])CCCCC.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH3:26])[C:21](=[O:27])[CH:20]=[CH:19]2>C1COCC1.CCCCCCC>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23]([N:22]([CH3:26])[C:21](=[O:27])[CH:20]3[CH2:7][CH:19]32)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 2204596-Methoxy-1-methyl-2(1H)-quinolinoneHCID 178506865HCID 178506865, compound

Product 1

HCID 21931845HCID 21931845, compoundYield 107.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 3.35 gm (15.1 mmol) trimethylsulfoxonium iodide in 10 ml of THF at 0° C. under nitrogen was treated portionwise with 5.8 ml (14.6 mmol) of 2.5 M n-hexyllithium in heptane over 30 minutes. The mixture was stirred for 30 minutes at 0° C. and then treated with 1.0 gm (5.02 mmol) 6-Methoxy-1-methyl-1H-quinolin-2-one followed by heating under reflux for 1.5 hours. The reaction mixture was allowed to cool to ambient temperature before quenching with 35 ml of water followed by extraction into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated to afford 1.1 gm of desired product. Mass spectrum APCI m/e 204 (p+1).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. temperatureto cool to ambient temperature
  4. custombefore quenching with 35 ml of water
  5. extractionfollowed by extraction into ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-64972da0117b461e92952d32eb6b5015
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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