Methyl iodide → 2(3H)-Benzofuranone, 3,3-dimethyl-

HRID 2070746Notes

Reaction equation

HRID 2070746 reaction equation
O1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][C:2]1=O.I[CH3:12].[C:13](=[O:16])([O-])[O-:14].[K+].[K+]>CN(C=O)C>[CH3:2][C:3]1([CH3:12])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:14][C:13]1=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 683822(3H)-Benzofuranone

Product 1

HCID 5956202(3H)-Benzofuranone, 3,3-dimethyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of benzofuran-2(3H)-one (20 g) dissolved in DMF (250 mL) was treated with iodomethane (33.4 mL) at 0° C. before adding potassium carbonate (134 g) portionwise over a period of 10 minutes under nitrogen. The resulting suspension was stirred at 25° C. for 3 days. The mixture was filtered and the solids washed with ethyl acetate. The filtrate was diluted with 2M hydrochloric acid, extracted with ethyl acetate. The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified (SiO2 chromatography eluting with 30% dichloromethane in iso-hexane). Pure fractions were evaporated to dryness to afford the subtitle compound (19.70 g). 1H NMR δ (CDCl3) 7.32-7.08 (m, 4H), 1.53 (s, 6H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids washed with ethyl acetate
  3. additionThe filtrate was diluted with 2M hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford crude product
  9. customThe crude product was purified
  10. wash(SiO2 chromatography eluting with 30% dichloromethane in iso-hexane)
  11. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-77341d5b1546471297a8edbe588031b3
Source dataset
uspto-grants-2012_10
Patent number
US08299246B2

Reaction notes

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