Methyl iodide → HCID 90021562, compound

HRID 1487859Notes

Reaction equation

HRID 1487859 reaction equation
[CH:1]1([C:4]2[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=2[C:13](=[O:16])[CH2:14][CH3:15])[CH2:3][CH2:2]1.[C:17](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH:1]1([C:4]2[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:17])=[O:9])=[CH:6][C:5]=2[C:13](=[O:16])[CH2:14][CH3:15])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 90021739HCID 90021739, compound2×

Product 1

HCID 90021562HCID 90021562, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
2.5 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 4-cyclopropyl-3-propanoylbenzoic acid (compound 10.6, 500 mg, 2.29 mmol) in N,N-dimethylformamide (20 mL) and potassium carbonate (633 mg, 4.55 mmol). The mixture was cooled to 0-5° C. then iodomethane (157 μL, 2.52 mmol) was added drop-wise. The resulting mixture was stirred for 1 h at 5-10° C., then quenched with water/ice (80 mL). The aqueous phase was extracted with ethyl acetate (2×150 mL) and the combined organic layers were washed with brine (20 mL), sodium carbonate (sat., 20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. Obtained 400 mg (75%) of the title compound as a light brown oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. customquenched with water/ice (80 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×150 mL)
  4. washthe combined organic layers were washed with brine (20 mL), sodium carbonate (sat., 20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94c26fcf408b47538a4380d7d620b4ff
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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